Carbohydrates and Conjugates ……………………… 248– 247 –

Carbohydrates

Carbohydrates
andConjugates

Carbohydrates and Conjugates
Code

CompoundPrice:Yen

22001

2,3,4,6-Tetra-O-Acetyl-α-D-Glucopyranosyl Fluoride-20

(M.W. 350.29)

C14H19O9F

1g
5g

15,00050,000[3934-29-0]

Glycosyl Donor (Glycosyl Fluoride)1) M. Hayashi, S Hashimoto, and R. Noyori, Chem. Lett., 1747 (1984).
2) W.A. Szarek, G. Grynkiewicz, B. Doboszewski, and G.W. Hay, Chem. Lett., 1751 (1984).
3) B. Ernst and T. Winkler, Tetrahedron Lett., 30, 3081 (1989).
4) S. Caddick, W.B. Motherwell, and J.A. Wilkinson, J. Chem. Soc. Chem. Commun., 674 (1991).

22002

2,3,4,6-Tetra-O-Acetyl-α-D-Galactopyranosyl Fluoride-20

(M.W. 350.29)

C14H19O9F

1g
5g

15,00050,000[4163-44-4]

Glycosyl Donor (Glycosyl Fluoride)1) W.A. Szarek, G. Grynkiewicz, B. Doboszewski, and G.W. Hay, Chem. Lett., 1751 (1984).
2) B. Ernst and T. Winkler, Tetrahedron Lett., 30, 3081 (1989).
3) S. Caddick, W.B. Motherwell, and J.A. Wilkinson, J. Chem. Soc. Chem. Commun., 674 (1991).

22003

2,3,4,6-Tetra-O-Acetyl-α-D-Mannopyranosyl Fluoride-20

(M.W. 350.29)

1g
5g

C14H19O9F

Glycosyl Donor (Glycosyl Fluoride)1) W.A. Szarek, G. Grynkiewicz, B. Doboszewski, and G.W. Hay, Chem. Lett., 1751 (1984).
2) B. Ernst and T. Winkler, Tetrahedron Lett., 30, 3081 (1989).
3) S. Caddick, W.B. Motherwell, and J.A. Wilkinson, J. Chem. Soc. Chem. Commun., 674 (1991).

– 248 –

15,00050,000Carbohydrates and Conjugates (continued)
Code

Compound22004

2-Deoxy-2-Phthalimido-3,4,6-Tri-O-Acetylα-D-Glucopyranosyl Fluoride-20

(M.W. 437.37)

Price:Yen
1g
5g

20,00065,0001g
5g

25,00080,0001g
5g

50,000200,000

C20H20NO9F

Glycosyl Donor (Glycosyl Fluoride)1) C. Unverzagt and H. Kunz, J. Prakt. Chem., Chem.-Ztg, 334, 570 (1992).

-20

2-Deoxy-2-Phthalimido-3,4,6-Tri-O-Acetylα-D-Galactopyranosyl Fluoride(M.W. 437.37)

C20H20NO9F

Glycosyl Donor (Glycosyl Fluoride)
22101
-20

Methyl (Methyl 5-Acetamido-4,7,8,9-TetraO-Acetyl-3,5-Dideoxy-2-Thio-D-GlyceroD-Galacto-2-Nonulopyranosid)onate(M.W. 521.54)

C21H31NO12S

Glycosyl Donor (Thioglycoside)1) I.M. Privalova and A.Y. Khorlin, Izv. Akad. Nauk SSSR, Ser. Khim., 2785 (1969).
2) O. Kanie, M. Kiso, and A. Hasegawa, J. Carbohydr. Chem., 7, 501 (1988).
3) T. Yamamoto, T. Teshima, U. Saitoh, M. Hoshi, and T. Shiba, Tetrahedron Lett., 35, 2701 (1994).

– 249 –

Carbohydrates

22005

Carbohydrates and Conjugates (continued)
Code

Compound

22102

Methyl 4,7,8,9-Tetra-O-Acetyl-3,5-Dideoxy5-(2,2,2-Trichloroethoxycarbonylamino)D-Glycero-D-Galacto-2-Nonulopyranosylonate-2N-Phenyltrifluoroacetimidate

-20

AcO

Price:Yen

OAc
OAc

500 mg1g

50,00080,000COOMe
O

TrocNH

Bulk

O

CF3
N

AcO

Ph

(M.W. 795.92)

C29H32N2O14Cl3F3

Glycosyl Donor (Phenyltrifluoroacetimidate)1) K. Tanaka, T. Goi, and K. Fukase, Synlett, 2958 (2005).
2) S. Tanaka, T. Goi, K. Tanaka, and K. Fukase, J. Carbohydr. Chem., 26, 369 (2007).

22103
-20

Fmoc-Ser[Ac4Galβ(1→3)Ac2GalNAcα(1→O)]

Bulk

25 mg

80,000

Bulk

25 mg

80,000O-β-2,3,4,6-Tetra-O-acetyl-D-galactopyranosyl-(1→3)-O-α-4,6di-O-acetyl-2-acetamido-2-deoxy-D-galactopyranosyl-(1→O)9-fluorenylmethoxycarbonyl-L-serine
AcO

OAc

AcO

OAc

O
AcO

O
O

OAc

AcNH
O

FmocNH(M.W. 944.88)

COOH

C44H52N2O21

Reagent for Mucin-Type O-Glycopeptide Synthesis
1) T. Reipen and H. Kunz, Synthesis, 2487 (2003).

22104
-20

Fmoc-Thr[Ac4Galβ(1→3)Ac2GalNAcα(1→O)]
O-β-2,3,4,6-Tetra-O-acetyl-D-galactopyranosyl-(1→3)-O-α-4,6di-O-acetyl-2-acetamido-2-deoxy-D-galactopyranosyl-(1→O)9-fluorenylmethoxycarbonyl-L-threonine
AcO

OAc

AcO

O
AcO

OAc
O

O
OAc

AcNH
O

FmocNH(M.W. 958.91)

CH3

COOH

C45H54N2O21

Reagent for Mucin-Type O-Glycopeptide Synthesis
1) C. Brocke and H. Kunz, Synthesis, 525 (2004).

– 250 –

Carbohydrates and Conjugates (continued)
Code

Compound

23001-v

5-Bromo-4-Chloroindol-3-yl 5-Acetamido-3,5-Dideoxyα-D-Glycero-D-Galacto-2-Nonulopyranosidonic Acid
[X-Neu5Ac, X-Sialic Acid, X-NANA]-20

Price:Yen
Vial

5 mg

10,000(Ammonium Form)

C19H22N2O9BrCl[265979-52-0]

Histochemical Substrate for Neuraminidase1) I. Fujii, Y. Iwabuchi, T. Teshima, T. Shiba, and M. Kikuchi, Bioorg. Med. Chem., 1, 147 (1993). (Original; Synthesis)– 251 –

Carbohydrates(M.W. 537.74)

Carbohydrates and Conjugates (continued)
Code

Compound

23002-v

2-[N-(7-Nitrobenz-2-Oxa-1,3-Diazol-4-yl)Amino]2-Deoxy-D-Glucose
2-NBDG-20

Price:Yen
Vial

0.5 mg

5,000

OH
O

HO

OH

HO
HN

NO2

N

N
O

(M.W. 342.26)

C12H14N4O8[186689-07-6]

Reagent for Monitoring Glucose Uptake into Single, Living Cells
1) K. Yoshioka, H. Takahashi, T. Homma, M. Saito, K.-B. Oh, Y. Nemoto, and H. Matsuoka,
Biochim. Biophys. Acta, 1289, 5 (1996). (Original)
2) K. Yamada, M. Nakata, N. Horimoto, M. Saito, H. Matsuoka, and N. Inagaki,
J. Biol. Chem., 275, 22278 (2000). (Measurement of Glucose Uptake in Living Mammalian Cells)3) K. Yamada, M. Saito, H. Matsuoka, and N. Inagaki, Nature Protocols, 2, 753 (2007).
(Chem. Synthesis & Protocols for Measurement)
4) J.V. Rocheleau, G.M. Walker, W.S. Head, O.P. McGuinness, and D.W. Piston,
Proc. Natl. Acad. Sci. U.S.A., 101, 12899 (2004). (Monitoring of Glucose Uptake in Islet)• This compound is distributed through Peptide Institute, Inc. under the license of Tokyo University of Agriculture andTechnology.

23003-v

New-20

2-[N-(7-Nitrobenz-2-Oxa-1,3-Diazol-4-yl)Amino]2-Deoxy-L-Glucose
2-NBDLGVial

0.5 mg15,000

HO
O

OH

HO

OH
NH

O2N

N

N
O

(M.W. 342.26)

C12H14N4O8[1092935-76-6]

Control Substrate for 2-NBDG
1) T. Yamamoto, Y. Nishiuchi, T. Teshima, H. Matsuoka, and K. Yamada, Tetrahedron Lett., 49, 6876 (2008).
(Chem. Synthesis)2) K. Yamada, M. Saito, H. Matsuoka, and N. Inagaki, Nature Protocols, 2, 753 (2007). (Protocols for Measurement)• This compound is distributed through Peptide Institute, Inc. under the license of Hirosaki University Graduate Schoolof Medicine, Tokyo University of Agriculture and Technology, and Peptide Institute, Inc.

– 252 –

Carbohydrates and Conjugates (continued)
Code

CompoundPrice:Yen

23005-sNew

UDP-β-L-Arabinofuranose
UDP-β-L-Araf-20

(Triethylammonium Form)

Vial

0.1 mg18,000Uridine-5'-diphospho-β-L-arabinofuranose
O
OH
O

O
O
OH

HO

P
OH

HN

O
O

P

O

O

OH
OH

(M.W. 536.28)

N

O

OH

C14H22N2O16P2

Reagent for Research in Arabinofuranose Biogenesis in Plants

24001-s-20

O-(Acetamido-3,5-Dideoxy-D-Glycero-α-D-GalactoVial
2-Nonulopyranosylonic Acid)-(2→3)-O-β-D-Galactopyranosyl(1→4)-O-β-D-Glucopyranosyl-(1→1)-(2S,3R,4E)-2-N(7-Nitrobenz-2-Oxa-1,3-Diazol-4-yl)Aminooctanamido4-Octadecene-1,3-diol[GM3 Labelled by NBD]

0.1 mg(Ammonium Form)(M.W. 1219.3)

C55H90N6O24

Synthetic ProductFluorescence Labelled Ganglioside
1) K. Akiyoshi, A. Itaya, S.M. Nomura, N. Ono, and K. Yoshikawa, FEBS Lett., 534, 33 (2003).
(Physicochemical Role of Gangliosides)– 253 –

20,000Carbohydrates

1) T. Konishi, H. Ono, M. Ohnishi–Kameyama, S. Kaneko, and T. Ishii, Plant Physiol., 141, 1098 (2006).
(Substrate for Arabinofuranosyltransferase)2) T. Konishi, T. Takeda, Y. Miyazaki, M. Ohnishi-Kameyama, T. Hayashi, M.A. O'Neill, and T. Ishii, Glycobiol., 17,345 (2007). (Use in Enzymatic Furanose-Pyranose Interconversion)3) Q. Zhang and H.-w. Liu, Bioorg. Med. Chem. Lett., 11, 145(2001). (Chem. Synthesis)

Carbohydrates and Conjugates (continued)****** Glycosidase Inhibitors ******
Code

CompoundPrice:Yen

24002-v

Siastatin B-20

(3S,4S,5R,6R)-6-(Acetylamino)-4,5-dihydroxy-3piperidinecarboxylic acid

Vial

5 mg

10,000

H
N
COOH
AcNH
HO
OH

(M.W. 218.21)

C8H14N2O5[54795-58-3]

Microbial Product

Inhibitor for Sialidase
1) H. Umezawa, T. Aoyagi, T. Komiyama, H. Morishima, M. Hamada, and T. Takeuchi, J. Antibiotics, 27, 963 (1974).
(Original)• This compound is distributed through Peptide Institute, Inc. under the technical and scientific advices of Microbial
Chemistry Research Foundation.

24003-v

Nojirimycin Bisulfite-20

5-Amino-5-deoxy-glucopyranose bisulfite(M.W. 243.23)

Vial

5 mg

4,800

C6H13NO7S

Microbial Product

Inhibitor for β -Glucosidase (Apricot Emulsin)
1) T. Niwa, S. Inouye, T. Tsuruoka, Y. Koaze, and T. Niida, Agric. Biol. Chem., 34, 966 (1970). (Original)

24004-v

D-Glucaro-δ-Lactam-20(Potassium Salt)(2S,3R,4S,5R)-3,4,5-Trihydroxy-6-oxo2-piperidinecarboxylic acid

(M.W. 191.14)

Vial

5 mg

6,500

C6H9NO6

Microbial Product

Inhibitor for Bovine Liver β -Glucuronidase
1) T. Niwa, T. Tsuruoka, S. Inouye, Y. Naito, T. Koeda, and T. Niida, J. Biochem., 72, 207 (1972). (Original)– 254 –

Carbohydrates and Conjugates (continued)****** Endotoxins (Synthetic) ******
Code

Compound

24005-s

Lipid A (E. coli)
Compound 506, LA-15-PP-20

Price:YenVial
HO
H2O3P OO

(Triethylammonium Form)

O

HO
O

NH

NH

O

O

OPO3H2
O

O
OH

O
O

O

OH
O

Carbohydrates

C94H178N2O25P2

20,000OO

2-Deoxy-6-O-{2-deoxy-2-[(R)-3-(dodecanoyloxy)
tetradecanoylamino]-3-O-[(R)-3-(tetradecanoyloxy)
tetradecanoyl]-β-D-glucopyranosyl}-3-O-[(R)-3hydroxytetradecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]α-D-glucopyranose 1,4'-diphosphate(M.W. 1798.4)

0.1 mg[95991-05-2]

Synthetic Product

Active Principle of Endotoxin
1) M. Imoto, S. Kusumoto, T. Shiba, E.Th. Rietschel, C. Galanos, and O. Luderitz, Tetrahedron Lett., 26, 907 (1985).
(Original; Chem. Structure)2) M. Imoto, H. Yoshimura, T. Shimamoto, N. Sakaguchi, S. Kusumoto, and T. Shiba, Bull. Chem. Soc. Jpn., 60, 2205
(1987). (Chem. Synthesis)

24006-s-20

Vial

Lipid IVa
Compound 406, LA-14-PP, Precursor Ia

0.1 mg20,000(Triethylammonium Form)

2-Deoxy-6-O-{2-deoxy-3-O-[(R)-3-hydroxytetradecanoyl]2-[(R)-3-hydroxytetradecanoylamino]-β-D-glucopyranosyl}3-O-[(R)-3-hydroxytetradecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-α-D-glucopyranose 1,4'-diphosphateHO
H2O3P O
O

O

O

O

HO
O

NH

O

O
O

OPO3H2
O

OH

OH
OH

(M.W. 1405.7)

NH

OH

C68H130N2O23P2

Synthetic Product

Biosynthetic Precursor of Lipopolysaccharide
1) M. Imoto, S. Kusumoto, T. Shiba, E.Th. Rietschel, C. Galanos, and O. Luderitz, Tetrahedron Lett., 26, 907 (1985).
(Original; Chem. Structure)2) M. Imoto, H. Yoshimura, M. Yamamoto, T. Shimamoto, S. Kusumoto, and T. Shiba, Bull. Chem. Soc. Jpn., 60, 2197
(1987). (Chem. Synthesis)– 255 –

Carbohydrates and Conjugates (continued)
Code

CompoundPrice:Yen

24008-s

Lipid A (Salmonella)-20

(Triethylammonium Form)

Vial

2-Deoxy-6-O-{2-deoxy-2[(R)-3-(dodecanoyloxy)tetradecanoylamino]-3-O[(R)-3-(tetradecanoyloxy)tetradecanoyl]-β-D-glucopyranosyl}2-[(R)-3-(hexadecanoyloxy)tetradecanoylamino]HO
3-O-[(R)-3-hydroxytetradecanoyl]H2O3P O
α-D-glucopyranose 1,4'-diphosphate
O

0.1 mg

O

O

O

HO
O

NH

O

O
O

NH
OPO3H2
O

OH

O
O

O

O
O

(M.W. 2036.8)

20,000O

C110H208N2O26P2

Synthetic Product

Active Principle of Endotoxin
1) U. Seydel, B. Lindner, H.-W. Wollenweber, and E.T. Rietschel, Eur. J. Biochem., 145, 505 (1984).
(Original; Chem. Structure)2) A.X. Tran, M.E. Lester, C.M. Stead, C.R.H. Raetz, D.J. Maskell, S.C. McGrath, R.J. Cotter, and M.S. Trent,
J. Biol. Chem., 280, 28186 (2005). (Pharmacol.)3) Y. Shi, M.J. Cromie, F.-F. Hsu, J. Turk, and E.A. Groisman, Mol. Microbiol., 53, 229 (2004). (Pharmacol.)4) H.S. Gibbons, S. Lin, R.J. Cotter, and C.R.H. Raetz, J. Biol. Chem., 275, 32940 (2000). (Pharmacol.)– 256 –

Carbohydrates and Conjugates (continued)
Code

CompoundPrice:Yen

24007-v

Antiproliferative Factor Sialoglycopeptide
Vial
50 µg
APF Sialoglycopeptide
Thr[Neu5Acα(2→3)Galβ(1→3)GalNAcα(1→O)]541-Frizzled 8 (541-549)

20,000-20

(Ammonium Form)

O-(Acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2→3)O-β-D-galactopyranosyl-(1→3)-O-α-2-acetamido-2-deoxy-D-galactopyranosyl-(1→O)Thr-Val-Pro-Ala-Ala-Val-Val-Val-Ala
HO

OH

COOH
HO

OH
O
AcNH

OH

O

OH
OH
O

OH
O

O
AcNH

OH

O

O
O
N
H
NH2

O

O
H
N

N
N
H
O

O

O
H
N

N
H

OH
O

C63H107N11O29

Synthetic ProductAntiproliferative Factor from Interstitial Cystitis Patients
For over 40 years, we have been engaged in synthesizing biologically active peptides with variable
post-translational modifications. Glycopeptides are included in our synthetic repertoire. These peptides
contain a carbohydrate moiety introduced through the side chain of Ser/Thr/Asn, which in turn, affects more orless its intrinsic activity. For the synthesis of glycopeptides, the knowledge of carbohydrate chemistry, as well asthat of peptide chemistry, is required.
Antiproliferative factor sialoglycopeptide was isolated from the bladder of the patients with interstitial
cystitis1). Recently, the peptide portion of this factor has been elucidated to correspond to (541-549) of the 6thtransmembrane region of frizzled 8. Simultaneously, the structure of the carbohydrate on the side chain of Thr
was determined to be a trisaccharide including sialic acid by a combination of biochemical and synthetic
approaches 2). Antiproliferative factor sialoglycopeptide exerts the following disease-related activities:i) inhibition of normal bladder epithelial cell growth, ii) inhibition of 3H-thymidine incorporation into the same
cell, and iii) decrease of heparin-binding epidermal growth factor (EGF)-like growth factor production, andiv) increase of EGF production. In addition to these, this glycopeptide inhibits a bladder carcinoma T24 cellproliferation. The peptide without the carbohydrate moiety was found to be inactive, strongly indicating thatthe carbohydrate attachment onto this peptide is critical for eliciting the activity.
1) S.K. Keay, C.-O. Zhang, J. Shoenfelt, D.R. Erickson, K. Whitmore, J.W. Warren, R. Marvel, and T. Chai, Urology, 57,
9 (2001). (Original; Antiproliferative Factor Sialoglycopeptide from Urine of Interstitial Cystitis Patients)
2) S.K. Keay, Z. Szekely, T.P. Conrads, T.D. Veenstra, J.J. Barchi, Jr., C.-O. Zhang, K.R. Koch, and C.J. Michejda, Proc.
Natl. Acad. Sci. U.S.A., 101, 11803 (2004). (Original; Structure & Pharmacol.)3) C.-O. Zhang, Z.-L. Li, and C.-Z. Kong, BioMed Central Urology 2005, 5:7 (article 7 from volume 5 of the journal
issued in 2005). (Pharmacol.)– 257 –

Carbohydrates(M.W. 1482.6)

O
H
N

N
H

Carbohydrates and Conjugates (continued)****** Other Carbohydrate Related Products ******
Code

CompoundPrice:Yen

4031-v

Adjuvant Peptide-20

N-Ac-Mur-Ala-D-Glu-NH2

Vial(Mur: Muramic acid)(M.W. 492.48)

0.5 mg3,500

HO

C19H32N4O11

O[53678-77-6]

HO
O
NHAc

HN

N
H

O

OH
CONH2

O
COOH

4031

Adjuvant Peptide-20

N-Ac-Mur-Ala-D-Glu-NH2 • 2H2O

Bulk

25 mg

70,000(Mur: Muramic acid)(M.W. 492.48 • 36.03)

C19H32N4O11 • 2H2O

[53678-77-6]

Muramyl Dipeptide
1) F. Ellouz, A. Adam, R. Ciorbaru, and E. Lederer, Biochem. Biophys. Res. Commun., 59, 1317 (1974). (Original)
2) S. Kotani, Y. Watanabe, F. Kinoshita, T. Shimono, I. Morisaki, T. Shiba, S. Kusumoto, Y. Tarumi, and K. Ikenaka,
Biken J., 18, 105 (1975). (Chem. Synthesis & Immun. Activity)

4082-v

Phosphoramidon-20

(Sodium Salt)

Vial

0.5 mg3,500

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

C23H34N3O10P

NH[36357-77-4]

O

Microbial Product

H
N

HO
P
O
H3C

O

OH
N
H
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.)• This compound is distributed through Peptide Institute, Inc. under the technical and scientific advices of Microbial
Chemistry Research Foundation.

– 258 –