Enzyme Inhibitors

EnzymeInhibitors

Enzyme Inhibitors ……………………………………… 178– 177 –

Enzyme Inhibitors
1) D. Leung, G. Abbenante, and D.P. Fairlie, J. Med. Chem., 43, 305 (2000).
"Protease Inhibitors: Current Status and Future Prospects"

CodeCompound3221-v

Ac-Asp-Asn-Leu-Asp-H (aldehyde)[Ac-DNLD-CHO]-20

Price:Yen
Vial

C20H31N5O10

20,000O

Acetyl-L-aspartyl-L-asparaginyl-L-leucyl-L-aspart-1-al(M.W. 501.49)

5 mg

O

OH

Synthetic Product

O

O
H
N

H
N

H

N
H

N
H
O

NH2

O

OH

O

O

Selective Inhibitor for Caspase-3 Designed by in silico Screening System
1) A. Yoshimori, R. Takasawa, and S. Tanuma, BMC Pharmacol., 4, 7 (2004).
2) S. Tanuma, R. Takasawa, and S. Tanuma, Biol. Pharm. Bull., 27, 968 (2004).

3194-v-20

Vial

Ac-Asp-Gln-Thr-Asp-H (aldehyde)[Ac-DQTD-CHO]

5 mg

25,000

Acetyl-L-aspartyl-L-glutaminyl-L-threonyl-L-aspart-1-al(M.W. 503.46)

C19H29N5O11

O

Synthetic Product

OH

OH

O

O

H
N
N
H

Inhibitor for Caspase-7/3(Deduced from the Cleavage Site of Focal Adhesion
Kinase and Gelsolin)

H
N
N
H

O

O
H

O

OH
O

O

NH2

1) L.-P. Wen, J.A. Fahrni, S. Troie, J.-L. Guan, K. Orth, and G.D. Rosen, J. Biol. Chem., 272, 26056 (1997).
2) S. Kothakota, T. Azuma, C. Reinhard, A. Klippel, J. Tang, K. Chu, T.J. McGarry, M.W. Kirschner, K. Koths,
D.J. Kwiatkowski, and L.T. Williams, Science, 278, 294 (1997).

3172-v-20

Vial

Ac-Asp-Glu-Val-Asp-H (aldehyde)[Ac-DEVD-CHO]
Acetyl-L-aspartyl-L-glutamyl-L-valyl-L-aspart-1-al(M.W. 502.47)

C20H30N4O11

5 mg

20,000O[184179-08-6]
OH

Synthetic Product

O

O

H
N
N
H

H
N
N
H

O

O
H

O

OH
O

Inhibitor for Caspase-3/7/8

OOH

1) D.W. Nicholson, A. Ali, N.A. Thornberry, J.P. Vaillancourt, C.K. Ding, M. Gallant, Y. Gareau, P.R. Griffin,
M. Labelle, Y.A. Lazebnik, N.A. Munday, S.M. Raju, M.E. Smulson, T.-T. Yamin, V.L. Yu, and D.K. Miller,
Nature, 376, 37 (1995).
2) M. Enari, R.V. Talanian, W.W. Wong, and S. Nagata, Nature, 380, 723 (1996).
3) N.A. Thornberry, T.A- Rano, E.P. Peterson, D.M. Rasper, T. Timkey, M. Garcia-Calvo, V.M. Houtzager,
P.A. Nordstrom, S. Roy, J.P. Vaillancourt, K.T. Chapman, and D.W. Nicholson, J. Biol. Chem., 272, 17907 (1997).

– 178 –

Enzyme Inhibitors (continued)
Code

Compound3192-v

Ac-Asp-Met-Gln-Asp-H (aldehyde)[Ac-DMQD-CHO]-20

Price:Yen
Vial

5 mg

30,000

Acetyl-L-aspartyl-L-methionyl-L-glutaminyl-L-aspart-1-al(M.W. 533.55)

C20H31N5O10S[259199-63-8]

NH2

O
OH
H
N

O
N
H

O
N
H

O

O

H
N

H
O

OH
O

S

Inhibitor for Caspase-3
1) A. Takahashi, H. Hirata, S. Yonehara, Y. Imai, K.-K. Lee, R.W. Moyer, P.C. Turner, P.W. Mesner, T. Okazaki,
H. Sawai, S. Kishi, K. Yamamoto, M. Okuma, and M. Sasada, Oncogene, 14, 2741 (1997).
2) H. Hirata, A. Takahashi, S. Kobayashi, S. Yonehara, H. Sawai, T. Okazaki, K. Yamamoto, and M. Sasada,J. Exp. Med., 187, 587 (1998).

3196-v-20

Vial

Ac-Ile-Glu-Thr-Asp-H (aldehyde)[Ac-IETD-CHO]

5 mg

20,000

Acetyl-L-isoleucyl-L-glutamyl-L-threonyl-L-aspart-1-al(M.W. 502.52)

C21H34N4O10[191338-86-0]

Synthetic Product

OH
O

O

H
N
N
H

N
H

O

O

H
N

H
O

OH
O

OH

O

Inhibitor for Caspase-8/6 and Granzyme B(Deduced from the Cleavage Site of Procaspase-3)
1) Z. Han, E.A. Hendrickson, T.A. Bremner, and J.H. Wyche, J. Biol. Chem., 272, 13432 (1997).
2) M. Garcia-Calvo, E.P. Peterson, B. Leiting, R. Ruel, D.W. Nicholson, and N.A. Thornberry, J. Biol. Chem.,
273, 32608 (1998).

3199-v-20

Vial

Ac-Leu-Glu-His-Asp-H (aldehyde)[Ac-LEHD-CHO]

5 mg

25,000(Trifluoroacetate Form)

Acetyl-L-leucyl-L-glutamyl-L-histidyl-L-aspart-1-al(M.W. 538.55)

N

C23H34N6O9

NH

Synthetic Product

O

O

H
N
N
H

H
N
N
H

O

O
H

O

OH
O

O

Inhibitor for Caspase-9

OH1) N.A. Thornberry, T.A. Rano, E.P. Peterson, D.M. Rasper, T. Timkey, M. Garcia-Calvo, V.M. Houtzager,
P.A. Nordstrom, S. Roy, J.P. Vaillancourt, K.T. Chapman, and D.W. Nicholson, J. Biol. Chem., 272, 17907 (1997).

– 179 –

Enzyme Inhibitors

O

Synthetic ProductEnzyme Inhibitors (continued)
Code

Compound3187-v

Ac-Trp-Glu-His-Asp-H (aldehyde)[Ac-WEHD-CHO]-20

Price:Yen
Vial

5 mg

20,000(Trifluoroacetate Form)

Acetyl-L-tryptophyl-L-glutamyl-L-histidyl-L-aspart-1-al(M.W. 611.60)

C28H33N7O9[189275-71-6]

Synthetic Product
N
NH
O

NH
O

H
N
N
H

N
H

O

O

H
N

H
O

OH
O

OH

O

Inhibitor for Caspase-1
1) T.A. Rano, T. Timkey, E.P. Peterson, J. Rotonda, D.W. Nicholson, J.W. Becker, K.T. Chapman, and N.A. Thornberry,Chem. Biol., 4, 149 (1997).
2) M. Garcia-Calvo, E.P. Peterson, B. Leiting, R. Ruel, D.W. Nicholson, and N.A. Thornberry, J. Biol. Chem.,
273, 32608 (1998).

3180-v-20

Vial

Ac-Tyr-Val-Ala-Asp-CH2Cl[Ac-YVAD-CMK]

5 mg

20,000(Acetyl-L-tyrosyl-L-valyl-L-alanyl-L-aspart-1-yl)chloromethane(M.W. 540.99)

C24H33N4O8Cl[178603-78-6]

OH

Synthetic Product
O

O

H
N
N
H

O

H
N
N
H

O

Cl

O

OH
O

Inhibitor for Caspases

1) Y.A. Lazebnik, S.H. Kaufmann, S. Desnoyers, G.G. Poirier, and W.C. Earnshaw, Nature, 371, 346 (1994).
2) M. Enari, H. Hug, and S. Nagata, Nature, 375, 78 (1995).
3) C.E. Milligan, D. Prevette, H. Yaginuma, S. Homma, C. Cardwell, L.C. Fritz, K.J. Tomaselli, R.W. Oppenheim, and
L.M. Schwartz, Neuron, 15, 385 (1995).
4) E. Fujita, T. Mukasa, T. Tsukahara, K. Arahata, S. Omura, and T. Momoi, Biochem. Biophys. Res. Commun.,
224, 74 (1996).

3165-v-20

Vial

Ac-Tyr-Val-Ala-Asp-H (aldehyde)[Ac-YVAD-CHO]
Acetyl-L-tyrosyl-L-valyl-L-alanyl-L-aspart-1-al(M.W. 492.52)

C23H32N4O8

5 mg

20,000OH[143313-51-3]

Synthetic Product

O

H
N
N
H

Inhibitor for Caspase-1

O

O

H
N
N
H

O
H

O

OH
O

1) N.A. Thornberry, H.G. Bull, J.R. Calaycay, K.T. Chapman, A.D. Howard, M.J. Kostura, D.K. Miller, S.M. Molineaux,
J.R. Weidner, J. Aunins, K.O. Elliston, J.M. Ayala, F.J. Casano, J. Chin, G.J.-F. Ding, L.A. Egger, E.P. Gaffney,
G. Limjuco, O.C. Palyha, S.M. Raju, A.M. Rolando, J.P. Salley, T.-T. Yamin, T.D. Lee, J.E. Shively, M. MacCross,
R.A. Mumford, J.A. Schmidt, and M.J. Tocci, Nature, 356, 768 (1992).
2) S.M. Molineaux, F.J. Casano, A.M. Rolando, E.P. Peterson, G. Limjuco, J. Chin, P.R. Griffin, J.R. Calaycay,
G.J.-F. Ding, T.-T. Yamin, O.C. Palyha, S. Luell, D. Fletcher, D.K. Miller, A.D. Howard, N.A. Thornberry, and
M.J. Kostura, Proc. Natl. Acad. Sci. U.S.A., 90, 1809 (1993).
3) M. Enari, R.V. Talanian, W.W. Wong, and S. Nagata, Nature, 380, 723 (1996).
4) M. Garcia-Calvo, E.P. Peterson, B. Leiting, R. Ruel, D.W. Nicholson, and N.A. Thornberry, J. Biol. Chem.,
273, 32608 (1998).

– 180 –

Enzyme Inhibitors (continued)
Code

Compound3166-v

Ac-Tyr-Val-Lys-Asp-H (aldehyde)[Ac-YVKD-CHO]-20

Price:Yen
Vial

5 mg

20,000NH2(Trifluoroacetate Form)
OH

Acetyl-L-tyrosyl-L-valyl-L-lysyl-L-aspart-1-al
C26H39N5O8[147821-01-0]

Synthetic Product

O

O

H
N
N
H

N
H

O

O

H
N

H
O

OH
O

Inhibitor for Caspase-1, Affinity Ligand for Caspase-1

1) N.A. Thornberry, H.G. Bull, J.R. Calaycay, K.T. Chapman, A.D. Howard, M.J. Kostura, D.K. Miller, S.M. Molineaux,
J.R. Weidner, J. Aunins, K.O. Elliston, J.M. Ayala, F.J. Casano, J. Chin, G.J.-F. Ding, L.A. Egger, E.P. Gaffney,
G. Limjuco, O.C. Palyha, S.M. Raju, A.M. Rolando, J.P. Salley, T.-T. Yamin, T.D. Lee, J.E. Shively, M. MacCross,
R.A. Mumford, J.A. Schmidt, and M.J. Tocci, Nature, 356, 768 (1992).
2) T.L. Graybill, R.E. Dolle, C.T. Helaszek, R.E. Miller, and M.A. Ator, Int. J. Pept. Protein Res., 44, 173 (1994).

3204-v-20

Vial

Ac-Val-Asp-Val-Ala-Asp-H (aldehyde)[Ac-VDVAD-CHO]

5 mg

30,000

Acetyl-L-valyl-L-aspartyl-L-valyl-L-alanylL-aspart-1-al(M.W. 543.57)

C23H37N5O10[194022-51-0]O

Synthetic Product
O

H
N
N
H

O

H
N
N
H
OH

O

OH

O

H
N
H

O

O

O

Inhibitor for Caspase-2
1) R.V. Talanian, C. Quinlan, S. Trautz, M.C. Hackett, J.A. Mankovich, D. Banach, T. Ghayur, K.D. Brady, andW.W. Wong, J. Biol. Chem., 272, 9677 (1997).

3182-v-20

Vial

Ac-Val-Glu-Ile-Asp-H (aldehyde)[Ac-VEID-CHO]

5 mg

20,000

Acetyl-L-valyl-L-glutamyl-L-isoleucyl-L-aspart-1-al(M.W. 500.54)

C22H36N4O9

Synthetic Product
O

O

H
N
N
H

H
N
N
H

O

O
H

O

OH
O

O

OH

Inhibitor for Caspase-61) H. Hirata, A. Takahashi, S. Kobayashi, S. Yonehara, H. Sawai, T. Okazaki, K. Yamamoto, and M. Sasada,J. Exp. Med., 187, 587 (1998).

AIP See Code 4374 Lys-Lys-Lys-Leu-Arg-Arg-Gln-Glu-Ala-Phe-Asp-Ala-Tyr on page 196– 181 –

Enzyme Inhibitors(M.W. 549.62)

Enzyme Inhibitors (continued)
Code

Compound3202-v

Ala-Ala-Phe-CH2Cl[AAF-CMK]-20

Price:Yen
Vial

5 mg

6,000

(Trifluoroacetate Form)(L-Alanyl-L-alanyl-L-phenylalanyl)chloromethane(M.W. 339.82)

C16H22N3O3Cl[102129-66-8]
O

Synthetic Product

H
N
H2N

N
H

Cl

O

O

Inhibitor for Tripeptidyl Peptidase II (Component of Giant Protease with Some
Proteasome Function), Chymotrypsin, and Chymase
1) R. Glas, M. Bogyo, J.S. McMaster, M. Gaczynska, and H.L. Ploegh, Nature, 392, 618 (1998).
2) E. Geier, G. Pfeifer, M. Wilm, M. Lucchiari-Hartz, W. Baumeister, K. Eichmann, and G. Niedermann, Science,
283, 978 (1999).
3) L.A. Johnson, K.E. Moon, and M. Eisenberg, Biochim. Biophys. Acta, 953, 269 (1988).

4095-v

Amastatin-20

[(2S,3R)-3-Amino-2-hydroxy-5-methylhexanoyl]L-valyl-L-valyl-L-aspartic acid
(M.W. 474.55)

Vial

C21H38N4O8[67655-94-1]

OH

0.5 mg

6,900

O

O

H
N

Synthetic Product

H
N
N
H

NH2

O

OH
O

OH
O

4095

Amastatin-20

[(2S,3R)-3-Amino-2-hydroxy-5-methylhexanoyl]L-valyl-L-valyl-L-aspartic acid
(M.W. 474.55)

Bulk

25 mg

99,300C21H38N4O8Synthetic Product

Inhibitor for Aminopeptidase A/PS and Leucyl Aminopeptidase
1) T. Aoyagi, H. Tobe, F. Kojima, M. Hamada, T. Takeuchi, and H. Umezawa, J. Antibiotics, 31, 636 (1978). (Original)
2) H. Tobe, H. Morishima, H. Naganawa, T. Takita, T. Aoyagi, and H. Umezawa, Agric. Biol. Chem., 43, 591 (1979).
(Structure & Chem. Synthesis)
3) P.M. Dando and A.J. Barrett, In, Enzyme 343.Aminopeptidase PS, Handbook of Proteolytic Enzymes,(A.J. Barrett, N.D. Rawlings, and J.F. Woessner, eds.), Academic Press, New York, 1998, (Inhibitory Activity)– 182 –

Enzyme Inhibitors (continued)****** Angiotensin I Converting Enzyme Inhibitors ******
Compound4009-v

Bradykinin-Potentiator B(Mamushi, Agkistrodon halys blomhoffii)
Pyr-Gly-Leu-Pro-Pro-Arg-Pro-Lys-Ile-ProPro-20

(M.W. 1182.4)

Price:Yen

C56H91N15O13

Vial

0.5 mg2,800
Enzyme Inhibitors

Code[30892-86-5]

Synthetic Product

Inhibitor for Peptidyl-Dipeptidase A, Kininase II, and ACE (Angiotensin I Converting Enzyme)
1) H. Kato and T. Suzuki, Biochemistry, 10, 972 (1971). (Original)

4010-v-20

Bradykinin-Potentiator C(Mamushi, Agkistrodon halys blomhoffii)
Pyr-Gly-Leu-Pro-Pro-Gly-Pro-Pro-Ile-ProPro(M.W. 1052.2)

C51H77N11O13

Vial

0.5 mg2,300[30953-20-9]

Synthetic Product

Inhibitor for Peptidyl-Dipeptidase A, Kininase II, and ACE (Angiotensin I Converting Enzyme)
1) H. Kato and T. Suzuki, Biochemistry, 10, 972 (1971). (Original)

4097-v-20

Des-Pro2-Bradykinin
Arg-Pro-Gly-Phe-Ser-Pro-Phe-Arg(M.W. 963.09)

C45H66N14O10

Vial

0.5 mg

2,800

Bulk

25 mg

43,000[80943-05-1]

Synthetic Product

4097
-20

Des-Pro2-Bradykinin
Arg-Pro-Gly-Phe-Ser-Pro-Phe-Arg • 2AcOH • 3H2O
(M.W. 963.09 • 120.10 • 54.05)

C45H66N14O10 • 2CH3COOH • 3H2O

Synthetic Product

Inhibitor for Peptidyl-Dipeptidase A, Kininase II, and ACE (Angiotensin I Converting Enzyme)1) M. Naruse, S. Tamanami, K. Shuto, S. Sakakibara, and T. Kimura, Chem. Pharm. Bull., 29, 3369 (1981). (Original)– 183 –

Enzyme Inhibitors (continued)
Code

CompoundPrice:Yen

4062-v

Antipain-20

(Hydrochloride Form)

Vial

0.5 mg3,500[(S)-1-Carboxy-2-phenylethyl]carbamoyl-L-arginyl-L-valylargininal(M.W. 604.70)

C27H44N10O6[37691-11-5]

Microbial Product
O
H
N

O

H
N

H
N
N
H

H

O
HO

O

O
NH

4062

Antipain-20[(S)-1-Carboxy-2-phenylethyl]carbamoyl-L-arginyl-L-valylargininal
monohydrochloride dihydrate(M.W. 604.70 • 36.46 • 36.03)

NH

HN

NH2

HN

Bulk

25 mg
100 mg

8,600
25,400NH2

C27H44N10O6 • HCl • 2H2O

Microbial Product

Inhibitor for Trypsin, u-PA, Papain, and Cathepsin A/B
1) H. Suda, T. Aoyagi, M. Hamada, T. Takeuchi, and H. Umezawa, J. Antibiotics, 25, 263 (1972). (Original)
2) S. Umezawa, K. Tatsuta, K. Fujimoto, T. Tsuchiya, H. Umezawa, and H. Naganawa, J. Antibiotics, 25, 267 (1972).
(Original; Chem. Structure)3) J. Chau, J. Biol. Chem., 258, 4434 (1983). (Inhibitory Activity)– 184 –

Enzyme Inhibitors (continued)****** Arphamenines (continued) ******
CompoundPrice:Yen

4149-v

Arphamenine B-20

(Sulfate Form)

Vial

C16H24N4O4

3,900

NH2

(2R,5S)-5-Amino-8-guanidino-4-oxo-2p-hydroxyphenylmethyloctanoic acid
(M.W. 336.39)

0.5 mgEnzyme Inhibitors

Code

O
OH

[103900-19-2]

HN

O

NH2

Microbial Product
NH

OH

4149

Arphamenine B-20

(2R,5S)-5-Amino-8-guanidino-4-oxo-2p-hydroxyphenylmethyloctanoic acid hemisulfate monohydrate

Bulk

C16H24N4O4 • 1/2 H2SO4 • H2O(M.W. 336.39 • 49.04 • 18.02)

25 mg
100 mg24,00087,000[144110-38-3]

Microbial Product

Inhibitor for Aminopeptidase B
1) H. Umezawa, T. Aoyagi, S. Ohuchi, A. Okuyama, H. Suda, T. Takita, M. Hamada, and T. Takeuchi, J. Antibiotics,
36, 1572 (1983). (Original; IC50)
2) S. Ohuchi, H. Suda, H. Naganawa, T. Takita, T. Aoyagi, H. Umezawa, H. Nakamura, and Y.Iitaka, J. Antibiotics,
36, 1576 (1983). (Original; Chem. Structure)3173-v-20

Vial

Biotinyl-Asp-Glu-Val-Asp-H (aldehyde)[Biotin-DEVD-CHO]

1 mg

10,000

Biotinyl-L-aspartyl-L-glutamyl-L-valyl-L-aspart-1-al(M.W. 686.73)

C28H42N6O12S

O[178603-73-1]

Synthetic Product
O

OH

O

NH

O

O

H
N

HN

H
N

N
H
S

N
H
O

H
OH

O
O
O

OH

Inhibitor for Caspase-3/7/8
1) D.W. Nicholson, A. Ali, N.A. Thornberry, J.P. Vaillancourt, C.K. Ding, M. Gallant, Y. Gareau, P.R. Griffin,
M. Labelle, Y.A. Lazebnik, N.A. Munday, S.M. Raju, M.E. Smulson, T.-T. Yamin, V.L. Yu, and D.K. Miller,
Nature, 376, 37 (1995).

– 185 –

Enzyme Inhibitors (continued)
Code

Compound3223-v

Bz-Arg-His-D-Asp-CH2Cl[Bz-RHd-CMK]-20

Price:Yen
Vial

5 mg

(d: D-Asp)(Trifluoroacetate Form)

20,000

HN

N(Benzoyl-L-arginyl-L-histidyl-D-aspart-1-yl)chloromethane(M.W. 563.01)

C24H31N8O6Cl

O

Synthetic Product

O
H
N

H
N

Cl

N
H
O

O

O

OH
HN

HN

NH2

Selective Inhibitor for D-Aspartyl Endopeptidase
1) T. Kinouchi, S. Ishiura, Y. Mabuchi, Y. Urakami-Manaka, H. Nishio, Y. Nishiuchi, M. Tsunemi, K. Takada,
M. Watanabe, M. Ikeda, H. Matsui, S. Tomioka, H. Kawahara, T. Hamamoto, K. Suzuki, and Y. Kagawa,
Biochem. Biophys. Res. Commun., 314, 730 (2004).
• This compound is produced by Peptide Institute, Inc. under the license of Japan Science and Technology Agency.

CA-074 See Code 4322 on page 188
CA-074 Me See Code 4323 on page 188
Caspase Inhibitors and Substrates See List of Inhibitors and Substrates for Various Proteases on page 141

4063-v-20

Chymostatin

Vial

0.5 mg

3,500

Bulk

25 mg
100 mg15,30052,000A mixture of type A, B, and C[(S)-1-Carboxy-2-phenylethyl]carbamoyl-α-[2-iminohexahydro4(S)-pyrimidyl]-(S)-glycyl-X-phenylalaninal
X: L-leucyl(type A), L-valyl(type B), L-isoleucyl(type C)[9076-44-2]

Microbial Product4063

Chymostatin-20

A mixture of type A, B, and C[(S)-1-Carboxy-2-phenylethyl]carbamoyl-α-[2-iminohexahydro4(S)-pyrimidyl]-(S)-glycyl-X-phenylalaninal
X: L-leucyl(type A), L-valyl(type B), L-isoleucyl(type C)[9076-44-2]

Microbial Product

Inhibitor for Chymotrypsin, Chymase, Papain, and Cathepsin B/G
1) H. Umezawa, T. Aoyagi, H. Morishima, S. Kunimoto, M. Matsuzaki, M. Hamada, and T. Takeuchi, J. Antibiotics,
23, 425 (1970). (Original)
2) K. Tatsuta, N. Mikami, K. Fujimoto, S. Umezawa, H. Umezawa, and T. Aoyagi, J. Antibiotics, 26, 625 (1973).
(Chem. Structure)3) R.L. Stein and A.M. Strimpler, Biochemistry, 26, 2611 (1987). (Inhibitory Activity)
4) L.A. Johnson, K.E. Moon, and M. Eisenberg, Biochim. Biophys. Acta, 953, 269 (1988). (Inhibitory Activity)– 186 –

Enzyme Inhibitors (continued)
Code

Compound4146-v

Cl-Ac-(OH)Leu-Ala-Gly-NH2-20

N-Chloroacetyl-N-hydroxy-L-leucylL-alanylglycine amide(M.W. 350.80)

Price:Yen
Vial
OH

O
H
N
N
H

O

Cl-Ac-(OH)Leu-Ala-Gly-NH2-20

N-Chloroacetyl-N-hydroxy-L-leucylL-alanylglycine amide

NH2
O

Bulk

25 mg
100 mg18,70048,600Vial

5 mg

10,000C13H23N4O5Cl

Synthetic Product

Inhibitor for P. aeruginosa Elastase
1) N. Nishino and J.C. Powers, J. Biol. Chem., 255, 3482 (1980). (Original)

3219-v-20

(3,5-Difluorophenylacetyl)-Ala-Phg-OBut[DAPT](3,5-Difluorophenylacetyl)-L-alanylL-2-phenylglycine t-butyl ester(M.W. 432.46)

C23H26N2O4F2[208255-80-5]

Synthetic Product

Inhibitor for γ -Secretase
1) H.F. Dovey, V. John, J.P. Anderson, L.Z. Chen, P. de Saint Andrieu, L.Y. Fang, S.B. Freedman, B. Folmer,
E. Goldbach, E.J. Holsztynska, K.L. Hu, K.L. Johnson-Wood, S.L. Kennedy, D. Kholodenko, J.E. Knops, L.H. Latimer,
M. Lee, Z. Liao, I.M. Lieberburg, R.N. Motter, L.C. Mutter, J. Nietz, K.P. Quinn, K.L. Sacchi, P.A. Seubert,
G.M. Shopp, E.D. Thorsett, J.S. Tung, J. Wu, S. Yang, C.T. Yin, D.B. Schenk, P.C. May, L.D. Altstiel, M.H. Bender,
L.N. Boggs, T.C. Britton, J.C. Clemens, D.L. Czilli, D.K. Dieckman-McGinty, J.J. Droste, K.S. Fuson, B.D. Gitter,
P.A. Hyslop, E.M. Johnstone, W-Y. Li, S.P. Little, T.E. Mabry, F.D. Miller, B. Ni, J.S. Nissen, W.J. Porter, B.D. Potts,
J.K. Reel, D. Stephenson, Y. Su, L.A. Shipley, C.A. Whitesitt, T. Yin, and J.E. Audia, J. Neurochem., 76, 173 (2001).
(Original; Functional γ -Secretase Inhibitor in Brain)
2) A.Y. Kornilova, C. Das, and M.S. Wolfe, J. Biol. Chem., 278, 16470 (2003).
(Comparison of in Cells and Cell-Free Activity)

4132-v-20

Diprotin A
Ile-Pro-Ile(M.W. 341.45)

C17H31N3O4

Vial

0.5 mg

1,800

Bulk

25 mg
100 mg

4,800
13,300[90614-48-5]

Synthetic Product

4132
-20

Diprotin A
Ile-Pro-Ile • H2O(M.W. 341.45 • 18.02)

C17H31N3O4 • H2O[90614-48-5]

Synthetic Product

Inhibitor for Dipeptidyl-Aminopeptidase IV
1) H. Umezawa, T. Aoyagi, K. Ogawa, H. Naganawa, M. Hamada, and T. Takeuchi, J. Antibiotics, 37, 422 (1984).
(Original; IC50 & Chem. Structure)– 187 –

Enzyme Inhibitors

Cl

4146

2,900

O

N

C13H23N4O5Cl

Synthetic Product(M.W. 350.80)

0.5 mgEnzyme Inhibitors (continued)****** E-64 and Related Inhibitors ******
Code

Compound4322-v

CA-074-20

[(2S,3S)-3-Propylcarbamoyloxirane-2-carbonyl]L-isoleucyl-L-proline(M.W. 383.44)

Price:Yen
Vial

C18H29N3O6

15,000O[134448-10-5]Synthetic Product

5 mg

O

N

H
N

N
H
OH

O
O

Inhibitor for Cathepsin BO1) M. Murata, S. Miyashita, C. Yokoo, M. Tamai, K. Hanada, K. Hatayama, T. Towatari, T. Nikawa, and N. Katunuma,
FEBS Lett., 280, 307 (1991). (Original; IC50)
2) T. Towatari, T. Nikawa, M. Murata, C. Yokoo, M. Tamai, K. Hanada, and N. Katunuma, FEBS Lett., 280, 311 (1991).
(Original; Pharmacol.)3) T. Inubushi, H. Kakegawa, Y. Kishino, and N. Katunuma, J. Biochem., 116, 282 (1994). (Biochem.)4323-v

CA-074 Me-20

[(2S,3S)-3-Propylcarbamoyloxirane-2-carbonyl]L-isoleucyl-L-proline methyl ester(M.W. 397.47)

Vial

C19H31N3O6

5 mg[147859-80-1]

15,000O

Synthetic Product

O

H
N

N
N
H

O

O

Proinhibitor for Intracellular Cathepsin B
Membrane Permeable Analog of CA-074

OO1) D.J. Buttle, M. Murata, C.G. Knight, and A.J. Barrett, Arch. Biochem. Biophys., 299, 377 (1992). (Original)– 188 –

Enzyme Inhibitors (continued)****** E-64 and Related Inhibitors (continued) ******

4096-v

E-64-20

[(2S,3S)-3-Carboxyoxirane-2-carbonyl]L-leucine (4-guanidinobutyl)amide(M.W. 357.41)

Price:Yen
Vial

C15H27N5O5

0.5 mg2,900

O[66701-25-5]O

Synthetic Product
HO

H
N

N
H
O

O

NH
N
H

4096

E-64

-20

[(2S,3S)-3-Carboxyoxirane-2-carbonyl]L-leucine (4-guanidinobutyl)amide hemihydrate

Bulk(M.W. 357.41 • 9.01)

C15H27N5O5 • 1/2 H2O

NH2

25 mg
100 mg1g

11,40028,500171,000[66701-25-5]

Synthetic Product

Inhibitor for Thiol Proteases
1) K. Hanada, M. Tamai, M. Yamagishi, S. Ohmura, J. Sawada, and I. Tanaka, Agric. Biol. Chem., 42, 523 (1978).
(Original)
2) K. Hanada, M. Tamai, S. Ohmura, J. Sawada, T. Seki and I. Tanaka, Agric. Biol. Chem., 42, 529 (1978).
(Structure & Chem. Synthesis)3) Y. Shoji-Kasai, M. Senshu, S. Iwashita, and K. Imahori, Proc. Natl. Acad. Sci. U.S.A., 85, 146 (1988). (Pharmacol.)4320-v

E-64-c-20

[(2S,3S)-3-Carboxyoxirane-2-carbonyl]L-leucine (3-methylbutyl)amide(M.W. 314.38)

Vial

C15H26N2O5

5 mg

10,000O[76684-89-4]

H
N

O

Synthetic Product

HO

N
H
O
O

Inhibitor for Thiol Protease (Cathepsin B/H/L and Calpain)
1) S. Hashida, T. Towatari, E. Kominami, and N. Katunuma, J. Biochem., 88, 1805 (1980). (Original; IC50)2) M. Tamai, K. Hanada, T. Adachi, K. Oguma, K. Kashiwagi, S. Omura, and M. Ohzeki, J. Biochem., 90, 255 (1981).
(Chem. Structure & Biochem.)
3) A. J. Barrett, A. A. Kembhavi, M. A. Brown, H. Kirschke, C. G. Knight, M. Tamai, and K. Hanada, Biochem. J.,
201, 189 (1982). (Biochem.)
4) K. Suzuki, J. Biochem., 93, 1305 (1983). (Biochem.)

4321-v

E-64-d-20

[(2S,3S)-3-Ethoxycarbonyloxirane-2-carbonyl]L-leucine (3-methylbutyl)amide(M.W. 342.43)

Vial

C17H30N2O5[88321-09-9]

5 mg

10,000O
HN

O

Synthetic Product
O

N
H
O
O

Inhibitor for Thiol Protease (Cathepsin B/H/L and Calpain)
Membrane Permeable Analog of E-64-c
1) M. Tamai, K. Matsumoto, S. Omura, I. Koyama, Y. Ozawa, and K. Hanada, J. Pharmacobio-Dyn., 9, 672 (1986).
(Original)
2) M. Tamai, C. Yokoo, M. Murata, K. Oguma, K. Sota, E. Sato, and Y. Kanaoka, Chem. Pharm. Bull., 35, 1098 (1987).
(Chem. Synthesis & Biochem.)– 189 –

Enzyme Inhibitors

CompoundEnzyme Inhibitors

CodeEnzyme Inhibitors (continued)****** Ebelactones ******
Code

Compound

4155

Ebelactone A-20

3,11-Dihydroxy-2,4,6,8,10,12-hexamethyl9-oxo-(E)-6-tetradecen-3-olide(M.W. 338.48)

Price:Yen
Bulk

C20H34O4

25 mg

100,000[76808-16-7]

Microbial Product

O

O

OH

O

Inhibitor for Esterase, Lipase, and N-Formylmethionine Aminopeptidase
1) H. Umezawa, T. Aoyagi, K. Uotani, M. Hamada, T. Takeuchi, and S. Takahashi, J. Antibiotics, 33, 1594 (1980).
(Original; IC50)2) K. Uotani, H. Naganawa, S. Kondo, T. Aoyagi, and H. Umezawa, J. Antibiotics, 35, 1495 (1982).
(Original; Chem. Structure)3) K. Uotani, H. Naganawa, T. Aoyagi, and H. Umezawa, J. Antibiotics, 35, 1670 (1982). (Biosynthetic Pathway)– 190 –

Enzyme Inhibitors (continued)
Compound4243-v

Elafin (Human)
Ala-Gln-Glu-Pro-Val-Lys-Gly-Pro-Val-SerThr-Lys-Pro-Gly-Ser-Cys-Pro-Ile-Ile-LeuIle-Arg-Cys-Ala-Met-Leu-Asn-Pro-Pro-AsnArg-Cys-Leu-Lys-Asp-Thr-Asp-Cys-Pro-GlyIle-Lys-Lys-Cys-Cys-Glu-Gly-Ser-Cys-GlyMet-Ala-Cys-Phe-Val-Pro-Gln-20

Price:Yen

Vial

20 µg

20,000

Enzyme Inhibitors

Code(Disulfide bonds between Cys16-Cys45,Cys23-Cys49,Cys32-Cys44,and Cys38-Cys53)(M.W. 5999.1)

C254H416N72O75S10

Synthetic Product

Elastase-Specific Inhibitor from Human Skin
1) O. Wiedow, J.-M. Schroder, H. Gregory, J.A. Young, and E. Christophers, J. Biol. Chem., 265, 14791 (1990).
(Original)
2) O. Wiedow, J.-M. Schroder, H. Gregory, J.A. Young, and E. Christophers, J. Biol. Chem., 266, 3356 (1991).
(Correction of Sequence)3) M. Tsunemi, H. Kato, Y. Nishiuchi, S. Kumagaye, and S. Sakakibara, Biochem. Biophys. Res. Commun.,
185, 967 (1992). (Chem. Synthesis & Biochem.)
4) M. Tsunemi, Y. Matsuura, S. Sakakibara, and Y. Katsube, Biochemistry, 35, 11570 (1996).
(Biochem.; Crystal Structure of Elafin-Pancreatic Elastase Complex)

4064-vElastatinal-20

Microbial Product4064

Elastatinal-20

Microbial ProductVial

0.5 mg

3,600

Bulk

25 mg
100 mg16,70057,600Inhibitor for Elastase1) H. Umezawa, T. Aoyagi, A. Okura, H. Morishima, T. Takeuchi, and Y. Okami, J. Antibiotics, 26, 787 (1973).
(Original)

4381-v

Epoxomicin-20(2R)-2-[Acetyl-(N-methyl-L-isoleucyl)-L-isoleucylL-threonyl- L-leucyl]-2-methyloxirane(M.W. 554.72)

Vial

C28H50N4O7

0.2 mg20,000[134381-21-8]

Synthetic Product

Inhibitor for Proteasome
1) L. Meng, R. Mohan, B.H.B. Kwok, M. Elofsson, N. Sin, and C.M. Crews, Proc. Natl. Acad. Sci. U.S.A.,
96, 10403 (1999). (Proteasome Inhibitor & Antiinflammatory Activity)
2) N. Sin, K.B. Kim, M. Elofsson, L. Meng, H. Auth, B.H.B. Kwok, and C.M. Crews, Bioorg. Med. Chem. Lett.,
9, 2283 (1999). (Proteasome Inhibitor)
3) K.B. Kim, J. Myung, N. Sin, and C.M. Crews, Bioorg. Med. Chem. Lett., 9, 3335 (1999). (Proteasome Inhibitor)
4) M. Groll, K.B. Kim, N. Kairies, R. Huber, and C.M. Crews, J. Am. Chem. Soc., 122, 1237 (2000).
(Crystal Structure of Proteasome Complex)– 191 –

Enzyme Inhibitors (continued)
Code4190-v-20

CompoundPrice:Yen
Vial

Foroxymithine

0.5 mg(M.W. 575.57)

C22H37N7O11[100157-28-6]

OOH

Microbial Product
O

OH
OH

H
N

HN

N

N

NH

N
H

O

O

O

N
H

4190
-20

6,500

(3S,6S )-3-(3-{N-[N-(N α-Acetyl-N δ-formylN δ-hydroxy-L-ornithyl)-L-seryl]N-(hydroxy)amino}propyl)-6-[3-(N-formylN-hydroxyamino)propyl]-2,5-piperazinedione

H

O

OH
O

Bulk

Foroxymithine

25 mg

90,500(3S,6S )-3-(3-{N-[N-(N α-Acetyl-N δ-formylN δ-hydroxy-L-ornithyl)-L-seryl]N-(hydroxy)amino}propyl)-6-[3-(N-formylN-hydroxyamino)propyl]-2,5-piperazinedione(M.W. 575.57)

C22H37N7O11[100157-28-6]

Microbial Product

Inhibitor for ACE (Angiotensin I Converting Enzyme)
1) H. Umezawa, T. Aoyagi, K. Ogawa, T. Obata, H. Iinuma, H. Naganawa, M. Hamada, and T. Takeuchi, J. Antibiotics,
38, 1813 (1985). (Original; Chem. Structure & IC50)
2) T. Aoyagi, T. Wada, H. Iinuma, K. Ogawa, F. Kojima, M. Nagai, H. Kuroda, A. Obayashi, and H. Umezawa,
J. Appl. Biochem., 7, 388 (1985). (Pharmacol.)D-Glucaro-δ-Lactam

See Code 24004 on page 254

3119

Gly-Gly-Tyr-Arg • AcOH • 2H2O

2～10

Glycylglycyl-L-tyrosyl-L-arginine(M.W. 451.48 • 60.05 • 36.03)

Bulk

0.1 g
1g

5,800
30,000C19H29N7O6 • CH3COOH •2H2O

Synthetic Product

Affinity Ligand for Papain
1) M.O. Funk, Y. Nakagawa, J. Skochdopole, and E.T. Kaiser, Int. J. Pept. Protein Res., 13, 296 (1979).

– 192 –

Enzyme Inhibitors (continued)****** KYT ******
Code

CompoundPrice:Yen

4395-v

KYT-1

-20

(Hydrochloride Form)

Vial

1 mg

25,000
Enzyme Inhibitors(3S)-N-[(1S)-5-Amino-1-(N,N-dimethylcarbamoyl)pentyl]3-{(2S)-6-amino-2-[(benzyloxycarbonyl)amino]hexanoylamino}6-guanidino-2-oxohexanamide(M.W. 619.76)

C29H49N9O6

Synthetic product

Inhibitor for Arg-Gingipain
1) T. Kadowaki, A. Baba, N. Abe, R. Takii, M. Hashimoto, T. Tsukuba, S. Okazaki, Y. Suda, T. Asao, and K.Yamamoto,Mol. Pharmacol., 66, 1599 (2004). (Original)• This compound is distributed through Peptide Institute, Inc. under the license of Prof. Kenji Ymamoto.

4396-v

KYT-36-20

(Hydrochloride Form)

Vial

1 mg

25,000(2S)-N-[(1S)-1-(4-Aminobutyl)-2-oxo-2-(N-benzylcarbamoyl)ethyl]N'-(N-methylphenylamino)-2-[(benzyloxycarbonyl)amino]pentane1,5-diamide(M.W. 630.73)

C34H42N6O6

Synthetic product

Inhibitor for Lys-Gingipain
1) T. Kadowaki, A. Baba, N. Abe, R. Takii, M. Hashimoto, T. Tsukuba, S. Okazaki, Y. Suda, T. Asao, and K.Yamamoto,Mol. Pharmacol., 66, 1599 (2004). (Original)• This compound is distributed through Peptide Institute, Inc. under the license of Prof. Kenji Ymamoto.

– 193 –

Enzyme Inhibitors (continued)
Code

Compound4394-v

L-685,458-20

[(2R,4R,5S)-2-Benzyl-5-(t-butyloxycarbonylamino)-4-hydroxy-6phenylhexanoyl]-L-leucyl-L-phenylalanine amide(M.W. 672.85)

Price:Yen
Vial

1 mg

30,000C39H52N4O6 [292632-98-5]

Synthetic Product

Inhibitor for γ -Secretase
1) Y.-M. Li, M. Xu, M.-T. Lai, Q. Huang, J.L. Castro, J. DiMuzio-Mower, T. Harrison, C. Lellis, A. Nadin, J.G. Neduvelil,
R.B. Register, M.K. Sardana, M.S. Shearman, A.L. Smith, X.-P. Shi, K.-C. Yin, J.A. Shafer, and S.J. Gardell,
Nature, 405, 689 (2000). (Biochem.; γ -Secretase Inhibitor)
2) Y.-M. Li, M.-T. Lai, M. Xu, Q. Huang, J. DiMuzio-Mower, M.K. Sardana, X.-P. Shi, K.-C. Yin, J.A. Shafer, and
S.J. Gardell, Proc. Natl. Acad. Sci. U.S.A., 97, 6138 (2000). (Biochem.; γ -Secretase Inhibitor)
3) M.S. Shearman, D. Beher, E.E. Clarke, H.D. Lewis, T. Harrison, P. Hunt, A. Nadin, A.L. Smith, G. Stevenson, andJ.L. Castro, Biochemistry, 39, 8698 (2000). (Biochem.; γ -Secretase Inhibitor)
4) G.Tian, C.D. Sobotka-Briner, J. Zysk, X. Liu, C. Birr, M.A. Sylvester, P.D. Edwards, C.D. Scott, and B.D. Greenberg,
J. Biol. Chem., 277, 31499 (2002). (Biochem.; Inhibition Mechanism)4368-v

Lactacystin-20

N-Acetyl-S-{(2R,3S,4R)-3-hydroxy-2[(1S)-1-hydroxy-2-methylpropyl]-4-methyl-5-oxopyrrolidine-2-carbonyl}-L-cysteine(M.W. 376.43)

Vial

C15H24N2O7S

0.2 mg

O

OH

O
NH

NH

[133343-34-7]

Microbial Product20,000

S

HO
HO

O
O

Inhibitor for Proteasome
1) S. Omura, T. Fujimoto, K. Otoguro, K. Matsuzaki, R. Moriguchi, H. Tanaka, and Y. Sasaki, J. Antibiotics,
44, 113 (1991). (Original)
2) S. Omura, K. Matsuzaki, T. Fujimoto, K. Kosuge, T. Furuya, S. Fujita, and A. Nakagawa, J. Antibiotics, 44, 117 (1991).
(Original; Chem. Structure)3) G. Fenteany, R.F. Standaert, W.S. Lane, S. Choi, E.J. Corey, and S.L. Schreiber, Science, 268, 726 (1995).
(Biochem.; Proteasome Inhibition)4) S. Imajoh-Ohmi, T. Kawaguchi, S. Sugiyama, K. Tanaka, S. Omura, and H. Kikuchi, Biochem. Biophys. Res.
Commun., 217, 1070 (1995). (Biochem.; Apoptotic Effect)• This compound is produced by Kyowa Medex Co., Ltd.

– 194 –

Enzyme Inhibitors (continued)
Code

Compound4249-v

Leuhistin-20

(2R,3S)-3-Amino-2-hydroxy-2-(1H-imidazol-4ylmethyl)-5-methylhexanoic acid
(M.W. 241.29)

Price:Yen
Vial

C11H19N3O3

0.5 mg

3,400
OH

H2N

OH

[129085-76-3]
NN
H

Inhibitor for Aminopeptidase M
1) T. Aoyagi, S. Yoshida, N. Matsuda, T. Ikeda, M. Hamada, and T. Takeuchi, J. Antibiotics, 44, 573 (1991).
(Original; IC50)
2) S. Yoshida, H. Nagasawa, T. Aoyagi, T. Takeuchi, Y. Takeuchi, and Y. Kodama, J. Antibiotics, 44, 579 (1991).
(Original; Chem. Structure)3) S. Yoshida, T. Aoyagi, and T. Takeuchi, J. Antibiotics, 44, 683 (1991). (Original; Biosynthesis)• This compoud is distributed exclusively through Peptide Institute, Inc. under the license of Microbial Chemistry
Research Foundation.

4041-v

Leupeptin-20

(Sulfate Form)

Vial

0.5 mg3,100

Acetyl-L-leucyl-L-leucyl-L-argininal(M.W. 426.55)

C20H38N6O4[55123-66-5]

OO

Microbial Product

H
N

H
N
H

N
H
O

O

NH
HN

4041

Leupeptin-20

Acetyl-L-leucyl-L-leucyl-L-argininal hemisulfate monohydrate

Bulk(M.W. 426.55 • 49.04 • 18.02)
C20H38N6O4 • 1/2 H2SO4 • H2O

25 mg
100 mg
1g

NH2

5,700
13,900111,200[103476-89-7]

Microbial Product

Inhibitor for Trypsin, Plasmin, Papain, and Cathepsin B
1) T. Aoyagi, T. Takeuchi, A. Matsuzaki, K. Kawamura, S. Kondo, M. Hamada, K. Maeda, and H. Umezawa,
J. Antibiotics, 22, 283 (1969). (Original)
2) T. Aoyagi, S. Miyata, M. Nanbo, F. Kojima, M. Matsuzaki, M. Ishizuka, T. Takeuchi, and H. Umezawa, J. Antibiotics,
22, 558 (1969). (Biological Activity)
3) S. Kondo, K. Kawamura, J. Iwanaga, M. Hamada, T. Aoyagi, K. Maeda, T. Takeuchi, and H. Umezawa,Chem. Pharm. Bull., 17, 1896 (1969). (Biological Activity)4) R.M. McConnell, J.L. York, D. Frizzell, and C. Ezell, J. Med. Chem., 36, 1084 (1993). (Inhibitory Activity)– 195 –

Enzyme InhibitorsO

Microbial ProductEnzyme Inhibitors (continued)
Code

Compound4374-v

Lys-Lys-Lys-Leu-Arg-Arg-Gln-Glu-Ala-PheVial
Asp-Ala-Tyr[Lys3,Phe10,Tyr13]-Autocamtide-2-Related Inhibitory Peptide (AIP)-20

(M.W. 1652.9)

Price:Yen
0.5 mg10,000

C74H121N23O20

Synthetic Product

Inhibitor for Calmodulin-Dependent Protein Kinase II
Calmodulin-dependent protein kinase II (CaMKII) is one of a number of second-messenger-responsive
multifunctional protein kinases, which responds to an increase in intracellular Ca2+. CaMKII exerts controlling
functions in many tissues and organs, especially in the central nervous system. AIP (autocamtide-2-related
inhibitory peptide), a potent inhibitor of CaMKII1), is a designed peptide based on the autophosphorylation site
in the autoinhibitory domain of the enzyme, where the phosphorylating Thr (at position 9 in AIP) is replaced byAla. Recent structure/activity study of AIP revealed that the substitution of Lys and Phe for Ala3 and Val10,
respectively, in AIP affords a stronger inhibitor with an IC50 value of 4.1 nM2). Inhibitory activity of the AIP
analog is specific for CaMKII because other enzymes of the family, protein kinase A, protein kinase C and
CaMKIV, were not inhibited or marginally suppressed by this inhibitor. This stronger inhibiting peptide, thus,
might be a useful reagent to study the physiological roles of CaMKII, such as neurotransmitter synthesis/release,long-term potentiation and formation of spatial learning.
1) A. Ishida and H. Fujisawa, J. Biol. Chem., 270, 2163 (1995). (AIP; Autocamtide-2-Related Inhibitory Peptide).
2) A. Ishida, Y. Shigeri, Y. Tatsu, K. Uegaki, I. Kameshita, S. Okuno, T. Kitani, N. Yumoto, and H. Fujisawa,
FEBS Lett., 427, 115 (1998). (Original)• This compoud is distributed through Peptide Institute, Inc. under the license of the Agency of Industrial Science &Technology.

4378-v-20

Lys-Thr-Glu-Glu-Ile-Ser-Glu-Val-Asn-StaVal-Ala-Glu-Phe

Vial

1 mg

20,000(Sta(Statine): (3S,4S)-4-Amino-3-hydroxy-6-methylheptanoic acid)(M.W. 1651.8)

C73H118N16O27[350228-37-4]

Synthetic ProductSta :Inhibitor for β -Secretase

N
H

OH

O

1) S. Sinha, J.P. Anderson, R. Barbour, G.S. Basi, R. Caccavello, D. Davis, M. Doan, H.F. Dovey, N. Frigon, J. Hong,
K. Jacobson-Croak, N. Jewett, P. Keim, J. Knops, I. Lieberburg, M. Power, H. Tan, G. Tatsuno, J. Tung, D. Schenk,
P. Seubert, S.M. Suomensaari, S. Wang, D. Walker, J. Zhao, L. McConlogue, and V. John, Nature, 402, 537 (1999).
(Original)

MG-115 See Code 3170 Z-Leu-Leu-Nva-H (aldehyde) on page 201
MG-132 See Code 3175 Z-Leu-Leu-Leu-H (aldehyde) on page 200
Nojirimycin Bisulfite See Code 24003 on page 254– 196 –

Enzyme Inhibitors (continued)
More soluble Pepstatin A (Code 4397-v / 4397) has released !

CodeCompound4397-v

Pepstatin A
Purity : higher than 90% (HPLC)-20

Price:Yen
Vial

C34H63N5O9

Microbial Product[26305-03-3]
O

O

O
H
N

N
H
O

-20

3,800

Isovaleryl-L-valyl-L-valyl[(3S,4S)-4-amino3-hydroxy-6-methylheptanoyl]-L-alanyl[(3S,4S)-4-amino-3-hydroxy-6-methylheptanoic acid](M.W. 685.89)4397

0.5 mg

H
N
OH

OH

O

Bulk

Pepstatin A
Purity : higher than 90% (HPLC)
Isovaleryl-L-valyl-L-valyl[(3S,4S)-4-amino3-hydroxy-6-methylheptanoyl]-L-alanyl[(3S,4S)-4-amino-3-hydroxy-6-methylheptanoic acid](M.W. 685.89)

C34H63N5O9

OH
N
H

N
H

25 mg
100 mg1g

O

7,000
17,000138,000[26305-03-3]

Microbial Product

Inhibitor for Pepsin, Cathepsin D/E, and Renin
1) H. Umezawa, T. Aoyagi, H. Morishima, M. Matsuzaki, M. Hamada, and T. Takeuchi, J. Antibiotics, 23, 259 (1970). (Original)
2) T. Aoyagi, H. Morishima, R. Nishizawa, S. Kunimoto, T. Takeuchi, H.Umezawa, and H. Ikezawa, J. Antibiotics,
25, 689 (1972). (Biological Activity)

4342-vPhebestin-20

(2S,3R)-3-Amino-2-hydroxy-4-phenylbutanoylL-valyl-L-phenylalanine(M.W. 441.52)

Vial

5 mg

10,000C24H31N3O5
OH

Synthetic Product

O
H
N

OH
N
H

NH2

Inhibitor for Aminopeptidase NOO1) M. Nagai, F. Kojima, H. Naganawa, M. Hamada, T. Aoyagi, and T. Takeuchi, J. Antibiotics, 50, 82 (1997). (Original)• This compound is distributed exclusively through Peptide Institute, Inc. under the license of Microbial Chemistry
Research Foundation.

– 197 –

Enzyme Inhibitors

In 2003, we started to distribute Pepstatin A of the purity "higher than 90%" when analyzed by
RP-HPLC (code 4397). This new item was welcomed by majority of customers. However, this accompanied
some complaints because of its low solubility. At the beginning, we thought this low solubility is the destiny of
the higher purity Pepstatin A. In striving to offer our customers satisfactory service, we continued to improve thesolubility of this item. Recently, we have succeeded to obtain both high purity Pepstatin A and higher solubility.
This new improved Pepstatin A is now available from us with easier handling.

Enzyme Inhibitors (continued)
Code

CompoundPrice:Yen

4082-v

Phosphoramidon-20

(Sodium Salt)

Vial

0.5 mg3,500

N-(α-Rhamnopyranosyloxyhydroxyphosphinyl)L-leucyl- L-tryptophan(M.W. 543.50)

C23H34N3O10P

NH
O[36357-77-4]

Microbial Product

H
N

HO

OH

P
O
H3C

N
H

O

O

O

HO
HO

4082

Phosphoramidon-20

N-(α-Rhamnopyranosyloxyhydroxyphosphinyl)L-leucyl- L-tryptophan disodium salt dihydrate

OH

Bulk

25 mg
100 mg

14,40048,500(M.W. 541.49 • 45.98 • 36.03)
C23H32N3O10P • 2Na • 2H2O

[119942-99-3]

Microbial Product

Inhibitor for Thermolysin, Neutral Endopeptidase-24.11(ANP Degradation Enzyme),
and Endothelin Converting Enzyme
1) H. Suda, T. Aoyagi, T. Takeuchi, and H. Umezawa, J. Antibiotics, 26, 621 (1973). (Original)
2) S.L. Stephenson and A.J. Kenny, Biochem. J., 243, 183 (1987). (Pharmacol.)3) B.P. Roques and A. Beaumont, Trends Pharmacol. Sci., 11, 245 (1990). (Review)4) Y. Matsumura, K. Hisaki, M. Takaoka, and S. Morimoto, Eur. J. Pharmacol., 185, 103 (1990). (Pharmacol.)PSI See Code 3169 Z-Ile-Glu(OBut )-Ala-Leu-H (aldehyde) on page 200
Siastatin B See Code 24002 on page 254
Sodium Potassium ATPase Inhibitor-1 (Porcine) See Code 4216 SPAI-1 (Porcine) on page 140

3214-v

SUAM-14746-20

3-({4-[2-(E)-Styrylphenoxy]butanoyl}-L-4-hydroxyprolyl)thiazolidine(M.W. 466.59)

Vial
C26H30N2O4S

5 mg

15,000HO

Synthetic Product
N

S

N
O

O
O

Inhibitor for Prolyl Endopeptidase1) M. Saito, M. Hashimoto, N. Kawaguchi, H. Shibata, H. Fukami, T. Tanaka, and N. Higuchi, J. Enzyme Inhib.,5, 51 (1991). (Assay Method )• This compound is distributed under the license of Suntory Limited.

TAPI-0 See Code INH-3850-PI on page 316
TAPI-1 See Code INH-3855-PI on page 316
TAPI–2 See Code INH-3852-PI on page 316– 198 –

Enzyme Inhibitors (continued)
Compound3207-v

Ubiquitin Aldehyde
Met*-Gln-Ile-Phe-Val-Lys-Thr-Leu-Thr-GlyLys-Thr-Ile-Thr-Leu-Glu-Val-Glu-Pro-SerAsp-Thr-Ile-Glu-Asn-Val-Lys-Ala-Lys-IleGln-Asp-Lys-Glu-Gly-Ile-Pro-Pro-Asp-GlnGln-Arg-Leu-Ile-Phe-Ala-Gly-Lys-Gln-LeuGlu-Asp-Gly-Arg-Thr-Leu-Ser-Asp-Tyr-AsnIle-Gln-Lys-Glu-Ser-Thr-Leu-His-Leu-ValLeu-Arg-Leu-Arg-Gly-Gly-H (aldehyde)-20Price:Yen
50 µg

Vial

20,000

Enzyme Inhibitors

Code* Met at position 1 is oxidized to Met(O).
(M.W. 8564.7)

C378H629N105O118S

Semi-synthetic Product

Inhibitor for Deubiquitinating Enzyme
1) J.R. Shaeffer and R.E. Cohen, Biochemistry, 35, 10886 (1996).
2) F. Melandri, L. Grenier, L. Plamondon, W.P. Huskey, and R.L. Stein, Biochemistry, 35, 12893 (1996).
3) S.H. Baek, K.S. Choi, Y.J. Yoo, J.M. Cho, R.T. Baker, K. Tanaka, and C.H. Chung, J. Biol. Chem., 272, 25560 (1997).
4) L.C. Dang, F.D. Melandri, and R.L. Stein, Biochemistry, 37, 1868 (1998).

3174-v

Z-Asp-CH2-DCB-20

(Benzyloxycarbonyl-L-aspart-1-yl)[(2,6-dichlorobenzoyl)oxy]methane(M.W. 454.26)

C20H17NO7Cl2

Vial

5 mg

[153088-73-4]

15,000O

Synthetic Product
O
O

OH
N
H

O

Cl

O
O
Cl

Inhibitor for Caspases
1) R.E. Dolle, D. Hoyer, C.V. Prasad, S.J. Schmidt, C.T. Helaszek, R.E. Miller, and M.A. Ator, J. Med. Chem.,
37, 563 (1994).
2) T. Mashima, M. Naito, S. Kataoka, H. Kawai, and T. Tsuruo, Biochem. Biophys. Res. Commun., 209, 907 (1995).

3189-v-20

Z-Glu-Lys(Biotinyl)-Asp-CH2-DMB
Vial[Z-EK(bio)D-aomk][Benzyloxycarbonyl-L-glutamyl-(N ε-biotinyl-L-lysyl)-L-aspart-1-yl][(2,6-dimethylbenzoyl)oxy]methane(M.W. 897.00)

O

C43H56N6O13S

1 mg

10,000OH
O

Synthetic Product
O

O

OH

O

H
N
O

N
H

N
H

O

O

O

S
HN

NH
O

HN
O

Affinity Ligand for Caspases
1) L.M. Martins, T. Kottke, P.W. Mesner, G.S. Basi, S. Shinha, N. Frigon, Jr., E. Tatar, J.S. Tung, K. Bryant, A. Takahashi,
P.A. Svingen, B.J. Madden, D.J. McCormick, W.C. Earnshaw, and S.H. Kaufmann, J. Biol. Chem., 272, 7421 (1997).
2) L.M. Martins, P.W. Mesner, T.J. Kottke, G.S. Basi, S. Sinha, J.S. Tung, P.A. Svingen, B.J. Madden, A. Takahashi,
D.J. McCormick, W.C. Earnshaw, and S.H. Kaufmann, Blood, 90, 4283, (1997).

– 199 –

Enzyme Inhibitors (continued)
Code

Compound3169-v

Z-Ile-Glu(OBut )-Ala-Leu-H (aldehyde)
[PSI]

-20

Price:Yen
Vial

5 mg

6,000

Benzyloxycarbonyl-L-isoleucyl-[(2S)-2-amino-4-(t-butyloxycarbonyl)butanoyl]L-alanyl- L-leucinal(M.W. 618.76)

C32H50N4O8[158442-41-2]

Synthetic Product

O

O

O
H
N

H
N
O

H

N
H

N
H
O

O

O

O

Inhibitor for Proteasome
1) M.E. Figueiredo-Pereira, K.A. Berg, and S. Wilk, J. Neurochem., 63, 1578 (1994).
2) E.B.-M. Traenckner, S. Wilk, and P.A. Baeuerle, EMBO J., 13, 5433 (1994).
3) M.E. Figueiredo-Pereira, W-E. Chen, H-M. Yuan, and S. Wilk, Arch. Biochem. Biophys., 317, 69 (1995).

3178-v

Z-Leu-Leu-H (aldehyde)-20

Benzyloxycarbonyl-L-leucyl-L-leucinal(M.W. 362.46)

Vial

5 mg

4,000

C20H30N2O4

Synthetic Product

O

O
H
N

O

N
H

H
O

Inhibitor for Calpain*
1) Y. Saito, S. Tsubuki, H. Ito, and S. Kawashima, Neurosci. Lett., 120, 1 (1990).
2) S. Tsubuki, Y. Saito, M. Tomioka, H. Ito, and S. Kawashima, J. Biochem., 119, 572 (1996).
* This compound does not inhibit Proteasome at the level of 10-6 M concentration.

3175-v-20

Vial

Z-Leu-Leu-Leu-H (aldehyde)[MG-132]

5 mg

4,000

Benzyloxycarbonyl-L-leucyl-L-leucyl-L-leucinal(M.W. 475.62)

C26H41N3O5[133407-82-6]

Synthetic Product

O

O
H
N

O

H
N
H

N
H
O

O

Inhibitor for Proteasome and Cathepsin K
1) Y. Saito, S. Tsubuki, H. Ito, and S. Kawashima, Neurosci. Lett., 120, 1 (1990).
2) T.J. Jensen, M.A. Loo, S. Pind, D.B. Williams, A.L. Goldberg, and J.R. Riordan, Cell, 83, 129 (1995).
3) B.J. Votta, M.A. Levy, A. Badger, J. Bradbeer, R.A. Dodds, I.E. James, S. Thompson, M.J. Bossard, T. Carr, J.R. Conner,
T.A. Tomaszek, L. Szewczuk, F.H. Drake, D.F. Veber, and M. Gowen, J. Bone Miner. Res., 12, 1396 (1997).
• This compound is distributed through Peptide Institute, Inc. under the license of Dr. H. Ito.

– 200 –

Enzyme Inhibitors (continued)
Code

Compound3218-v(Z-Leu-Leu-NHCH2)2CO[(Z-LL)2 Ketone]-20

Price:Yen
Vial

5 mg

7,000

1,3-Bis[(benzyloxycarbonyl-L-leucyl-L-leucyl)amino]acetone(M.W. 809.00)

C43H64N6O9[313664-40-3]

Enzyme Inhibitors

Synthetic Product

Inhibitor for Signal Peptide Peptidase
1) A. Weihofen, M.K. Lemberg, H.L. Ploegh, M. Bogyo, and B. Martoglio, J. Biol. Chem., 275, 30951 (2000). (Original)
2) A. Weihofen, K. Binns, M.K. Lemberg, K. Ashman, and B. Martoglio, Science, 296, 2215 (2002).
(Signal Peptide Peptidase Inhibitor)
3) A. Weihofen, M.K. Lemberg, E. Friedmann, H. Rueeger, A. Schmitz, P. Paganetti, G. Rovelli, and B. Martoglio,
J. Biol. Chem., 278, 16528 (2003). (Signal Peptide Peptidase Inhibitory Activity)

3170-v-20

Vial

Z-Leu-Leu-Nva-H (aldehyde)[MG-115]

5 mg

4,000

Benzyloxycarbonyl-L-leucyl-L-leucyl-L-norvalinal(M.W. 461.59)

C25H39N3O5[133407-86-0]

Synthetic Product

O

O
H
N

O

H
N
H

N
H
O

O

Inhibitor for Proteasome
1) Y. Saito, S. Tsubuki, H. Ito, and S. Kawashima, Neurosci. Lett., 120, 1 (1990).
2) A. Vinitsky, C. Michaud, J.C. Powers, and M. Orlowski, Biochemistry, 31, 9421 (1992).
3) K.L. Rock, C. Gramm, L. Rothstein, K. Clark, R. Stein, L. Dick, D. Hwang, and A.L. Goldberg, Cell, 78, 761 (1994).
4) V.J. Palombella, O.J. Rando, A.L. Goldberg, and T. Maniatis, Cell, 78, 773 (1994).
• This compound is distributed through Peptide Institute, Inc. under the license of Dr. H. Ito.

3188-v-20

Vial

Z-Val-Ala-Asp(OMe)-CH2F[Z-VAD-FMK]

1 mg

10,000{Benzyloxycarbonyl-L-valyl-L-alanyl-[(2S)2-amino-3-(methoxycarbonyl)propionyl]}
fluoromethane(M.W. 467.49)

C22H30N3O7F

Synthetic Product

Inhibitor for Caspases
1) E.A. Slee, H. Zhu, S.C. Chow, M. MacFarlane, D.W. Nicholson, and G.M. Cohen, Biochem. J., 315, 21 (1996).
2) H. Zhu, H.O. Fearnhead, and G.M. Cohen, FEBS Lett., 374, 303 (1995).

– 201 –

– 202 –