Biologically Active Peptides
APETx2
Code

Compound4472-sAPETx2(Sea Anemone, Anthopleura elegantissima)
Gly-Thr-Ala-Cys-Ser-Cys-Gly-Asn-Ser-LysGly-Ile-Tyr-Trp-Phe-Tyr-Arg-Pro-Ser-CysPro-Thr-Asp-Arg-Gly-Tyr-Thr-Gly-Ser-CysArg-Tyr-Phe-Leu-Gly-Thr-Cys-Cys-Thr-ProAla-Asp

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0.1 mg25,000(Reported disulfide bonds between Cys4-Cys37, Cys6-Cys30, Cys20-Cys38)(M.W. 4561.0) C196H280N54O61S6
Purity ≧99.0% (HPLC)[713544-47-9]

Selective Blocker of Acid-Sensing Ion Channel, ASIC3
Tissue acidosis is a common feature of many painful conditions. Protons are initially released by injured
tissues, and this leads to pain. Acid-sensing ion channels (ASICs) are excitatory cation channels directly gatedby extracellular protons, and composed of several isoforms which assemble into functional homo- andheteromeric tetramers. These channels are activated in response to the extracellular pH drop and involved innumerous functions including pain caused by acidosis1,2). A specific inhibitor of an individual ASIC is required
to discriminate a particular ASIC from others and to understand its function. Psalmotoxin 1 (Code 4435-s) is a
peptidic inhibitor specific to homomeric ASIC1a. APETx2, another peptidic toxin isolated from the sea
anemone Anthopleura elegantissima, is classified into the ASIC3-specific inhibitor3). APETx2 is a 42-residue
peptide with three disulfide linkages in a I-V, II-IV, and III-VI cysteine arrangement (cysteine numbering fromthe amino-terminus)3) and a member of the disulfide-rich all-β-structural family peptides4).
APETx2 shows a reversible inhibition of ASIC3-evoked peak current in an isoform-dependent manner3,5); forrat channels IC50 values are 63 nM (homomeric ASIC3), 117 nM (heteromeric ASIC2b-3), and for humanchannels IC50 value is 175 nM (homomeric ASIC3). APETx2-elicited functions through ASIC3 inhibition
include; i) suppression of postoperative6), acid-induced muscle7), and inflammatory7,8) pain and thus exerting
analgesic effects in rat and ii) increase of insulin resistance and regulation of anxiety in mouse9), whereas someadverse effects are suggested in association with the blockade of ASIC39). APETx2 as well as Psalmotoxin 1 are
obviously indispensable tools to be used in the research of ASIC-associated pain. Both peptides are available
from Peptide Institute, Inc. In addition to these ASIC blocker, novel mambalgin-1 (Code 4473-s) has been listed
recently as our items.
1) Z.-G. Xiong, G, Pignataro, M. Li, S.-y. Chang and R.P. Simon, Curr. Opin. Pharmacol., 8, 25 (2008). (Review)2) E. Deval, X. Gasull, J. Noel, M. Salinas, A. Baron, S. Diochot, and E. Lingueglia, Pharmacol. Ther., 128, 549 (2010).
(Review; Implication of ASIC3 in Pain)
3) S. Diochot, A. Baron, L.D. Rash, E. Deval, P. Escoubas, S. Scarzello, M. Salinas, and M. Lazdunski,
EMBO J., 23, 1516 (2004). (Original; Primary Structure, S-S Bond & Pharmacol.)4) B. Chagot, P. Escoubas, S. Diochot, C. Bernard, M. Lazdunski, and H. Darbon, Protein Sci., 14, 2003 (2005).
(NMR Structure)5) S. Diochot, M. Salinas, A. Baron, P. Escoubas, and M. Lazdunski, Toxicon, 49, 271 (2007). (Pharmacol.)6) E. Deval, J. Noel, X. Gasull, A. Delaunay, A. Alloui, V. Friend, A. Eschalier, M. Lazdunski, and E. Lingueglia,
J. Neurosci., 31, 6059 (2011). (Pharmacol.)7) J. Karczewski, R.H. Spencer, V.M. Garsky, A. Liang, M.D. Leitl, M.J. Cato, S.P. Cook, S. Kane and M.O. Urban,
Br. J. Pharmacol., 161, 950 (2010). (Pharmacol.)8) E. Deval, J. Noel, N. Lay, A. Alloui, S. Diochot, V. Friend, M. Jodar, M. Lazdunski, and E. Lingueglia, EMBO J., 27,3047 (2008). (Pharmacol.)9) W.-L. Wu, C.-F. Cheng, W.-H. Sun, C.-W. Wong, and C.-C. Chen, Pharmacol. Ther., 134, 127 (2012).
(Review; Pharmacol.)–1 –Mambalgin-1
CodeCompound4473-sMambalgin-1(Black Mamba, Dendroaspis polylepis polylepis)
Leu-Lys-Cys-Tyr-Gln-His-Gly-Lys-Val-ValThr-Cys-His-Arg-Asp-Met-Lys-Phe-Cys-TyrHis-Asn-Thr-Gly-Met-Pro-Phe-Arg-Asn-LeuLys-Leu-Ile-Leu-Gln-Gly-Cys-Ser-Ser-SerCys-Ser-Glu-Thr-Glu-Asn-Asn-Lys-Cys-CysSer-Thr-Asp-Arg-Cys-Asn-Lys

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0.1 mg30,000(Reported disulfide bonds between Cys3-Cys19, Cys12-Cys37, Cys41-Cys49, and Cys50-Cys55)(M.W. 6554.5)

C272H429N85O84S10 [1401381-87-0]
Purity ≧99.0% including Met (O) analog (≦1.0%) (HPLC)

Analgesic Peptide Targeting to Acid-Sensing Ion Channels
It is well-established that acid-sensing ion channels (ASICs) are essential regulators/modulators in thesensory peripheral pain pathways, thus making blockers of these channels potential analgesic reagents forresearch of pain management/treatment. The disulfide rich peptide toxins, psalmotoxin 1 (Code 4435-s) andAPETx2 (Code 4472-s), are examples of blockers which target and inhibit ASIC1a and ASIC3, respectively.
Recently, a novel blocker of ASICs called mambalgin-11) was isolated from the venom of the black mamba,
Dendroaspis polylepis polylepis; this 57-residue peptide is stabilized by four disulfide linkages in a I-III, II-IV, VVI, and VII-VIII cysteine arrangement (cysteine numbering from the amino-terminus), which is proposed basedon computer modeling experiments and subsequently confirmed by NMR structure analysis2). Results of thesequence alignment with other snake venom toxins and secondary structure prediction suggest that mambalgin-1
belongs to a member of snake three-finger toxins.
The specificity values of blocking expressed ASICs by mambalgin-1 are as follows; i) IC50 values for human
ASICs are 127 nM (homomeric ASIC1a) and 674 nM (heteromeric ASIC1a-2a), and those for rat ASICs are 55
nM (homomeric ASIC1a), 246 nM (heteromeric ASIC1a-2a), 61 nM (heteromeric ASIC1a-2b), 192 nM(homomeric ASIC1b), and 72 nM (heteromeric ASIC1a-1b), ii) homomeric ASIC2a and ASIC3-containing
channels are not inhibited, and iii) TRPV1, Nav1.8, Cav3.2, Kv1.2, P2X2, and 5-HT3A are also unaffected. In
addition to these experiments, mambalgin-1 was found to block native ASIC currents in the central nervous
system (CNS) and peripheral neurons in mouse. Analgesic effect was the consequence of the central or
peripheral injection of mambalgin-1 to mouse (0.34 nmol), which was as potent as that of morphine but
insensitive to naloxone.
Mambalgin-1 seems to be an effective pain-killing reagent without adverse effects of morphine, therefore,
further experimental research using synthetic mambalgin-1 may help to develop a novel analgesic agent.
1) S. Diochot, A. Baron, M. Salinas, D. Douguet, S. Scarzello, A.-S. Dabert-Gay, D. Debayle, V. Friend, A. Alloui,
M. Lazdunski, and E. Lingueglia, Nature, 490, 552 (2012). (Original)
2) M. Pan, Y. He, M. Wen, F. Wu, D. Sun, S. Li, L. Zhang, Y. Li, and C. Tian, Chem. Commun., 50, 5837 (2014).
(NMR Structure & S-S Bond)–2 –Angiotensin and Related Peptides
Code

Compound4474-v

Angiotensin A[Ala1]-Angiotensin II(Human)Ala-Arg-Val-Tyr-Ile-His-Pro-Phe

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(M.W. 1002.2) C49H71N13O10
Purity ≧99.0% (HPLC)

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0.5 mg3,000[51833-76-2]

Novel Form of Angiotensin II
Angiotensin II (Human) (Code 4001-v) is a major component in the renin-angiotensin system and influences
many biological functions in the cardiovascular system. A novel angiotensin II-related peptide named
angiotensin A was identified in human plasma by mass spectrometry1). Angiotensin A is similar to angiotensin
II, but with Asp-to-Ala substituted at position 1, and is most likely generated from angiotensin II by adecarboxylase. For end-stage renal failure patients, plasma concentration of angiotensin A has been found tobe higher than that of healthy subjects (5.1-73.6% vs. 2.1-25.2% of the angiotensin II concentration).
Angiotensin A shows a higher affinity to the angiotensin II type 2 (AT2) receptor than angiotensin II, whereas
the affinity of this peptide to the AT1 is the same as that of angiotensin II. Considering the facts that:i) angiotensin A elicits lower vasoconstricting activity than angiotensin II in the isolated perfused rat kidney andii) angiotensin A-induced hypertensive response is achieved at almost 10 times higher concentration thanangiotensin II-induced hypertensive response, along with results from some experiments using receptorselective antagonists, angiotensin A has been shown to be a partial agonist of the AT1A receptor. The ratio ofangiotensin A versus angiotensin II is relatively large and shown to increase in renal failure patients. Therefore,
angiotensin A may be essential for evaluating the angiotensin-induced biological functions in humans and otheranimals. In a Langendorff-prepared heart of a rat, an infusion of angiotensin A caused a significant reduction in
the coronary flow2). Angiotensin II elicited an increase in the duration of ischemia/reperfusion arrhythmias
while angiotensin A had no effect on cardiac rhythm during reperfusion2).
1) V. Jankowski, R. Vanholder, M. van der Giet, M. To
lle, S. Karadogan, J. Gobom, J. Furkert, A. Oksche, E. Krause,
T. N. A. Tran, M. Tepel, M. Schuchardt, H. Schluter, A. Wiedon, M. Beyermann, M. Bader, M. Todiras, W. Zidek,
and J. Jankowski, Arterioscler. Thromb. Vasc. Biol., 27, 297 (2007). (Original)
2) D.C. Coutinho, G. Foureaux, K.D. Rodrigues, R.L. Salles, P.L. Moraes, T.M. Murça, M.L. De Maria, E.R. Gomes,
R.A. Santos, S. Guatimosim, and A.J. Ferreira, J. Renin-Angiotensin-Aldosterone Syst.,
DOI:10.1177/1470320312474856 (Pharmacol.)–3 –Angiotensin and Related Peptides (continued)
Code

Compound4475-vAlamandine[Ala1]-Angiotensin (1-7), Angiotensin A (1-7)(Human, Rat, Mouse)
Ala-Arg-Val-Tyr-Ile-His-Pro

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(M.W. 855.00) C40H62N12O9
Purity ≧99.0% (HPLC)

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0.5 mg

3,000[1176306-10-7]

Novel Form of Angiotensin (1-7)
Angiotensin (1-7) (Code 4332-v), which is generated from angiotensin II by the action of angiotensin
converting enzyme 2 (ACE2), is an endogenous peptide that shows the opposite effects of angiotensin II, such as
vasodilation and antihypertensive activity.
When substituting Ala for Asp at position 1 in angiotensin (1-7), the resulting peptide named alamandine,
was discovered in early 2013 as a novel peptide of the renin-angiotensin system1). Alamandine is generated
through dual pathways: one from angiotensin A (Code 4474-v) by ACE2, and another from angiotensin (1-7) bydecarboxylation at the side chain of Asp. Alamandine shows similar biological functions to angiotensin (1-7):i) vasodilation at nM range, ii) a vasopressor effect in SHR (50 μg/kg) by oral administration of β-hydroxypropyl
cyclodextrin complex, and iii) antifibrosis in rats (50 μg/kg). These functions of alamandine are expressed
through Mas-related G-protein-coupled receptor member D (MrgD), but not through Mas and angiotensin II
type 2 receptors, to which angiotensin (1-7) interacts and exerts its biological activities2).
The novel endogenous peptide alamandine will help understand the physiological roles of angiotensin (1-7)
and related peptides more thoroughly and precisely.
1) R.Q. Lautner, D.C. Villela, R.A. Fraga-Silva, N. Silva, T. Verano-Braga, F. Costa-Fraga, J. Jankowski, V. Jankowski,
F. Sousa, A. Alzamora, E. Soares, C. Barbosa, F. Kjeldsen, A. Oliveira, J. Braga, S. Savergnini, G. Maia, A.B. Peluso,
D. Passos-Silva, A. Ferreira, F. Alves, A. Martins, M. Raizada, R. Paula, D. Motta-Santos, F. Klempin, A. Pimenta,
N. Alenina, R. Sinisterra, M. Bader, M.J. Campagnole-Santos, and R.A.S. Santos, Circ. Res., 112, 1104 (2013).
(Original)
2) D.C. Villela, D.G. Passos-Silva, and R.A. Santos, Curr. Opin. Nephrol. Hypertens., 23, 130 (2014). (Review)–4 –Angiotensin and Related Peptides (continued)
Code

Compound4476-v[Sar1, Ile4,8]-Angiotensin II
SII
Sar-Arg-Val-Ile-Ile-His-Pro-Ile

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(M.W. 918.14) C43H75N13O9
Purity ≧99.0% (HPLC)

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0.5 mg

3,000[185461-45-4]

β -Arrestin Selective Angiotensin II Type 1A Receptor Agonist
It has been discovered that activation of a G-protein-coupled receptor (GPCR) by a ligand follows two
distinct signaling pathways: G-protein-dependent and G-protein-independent signaling. In the latter case,downstream signaling is associated with the recruitment of the scaffolding protein β-arrestin. Binding of
β-arrestin to the receptor desensitizes the activated receptor, promotes the receptor internalization, andfunctionally activates the G-protein-independent signaling. Thus, it is possible to segregate the signaling
independence from dependency on G-protein by using a specific ligand, "biased agonist". A biased agonist is aligand involved in the G-protein-independent signaling, whereas it is characterized as an antagonist against the
G-protein-mediated functions.
In the renin-angiotensin system (RAS), angiotensin II (Code 4001-v) is a ligand of the angiotensin II type 1A
receptor (AT1AR) and shows various functional roles such as regulation of blood pressure and water intake. In
RAS, the synthetic angiotensin II analog, [Sar1,Ile4,8]-angiotensin II (SII) is a well-known prototypical biased
agonist of AT1AR1). Many papers researching SII have been published, such as those referenced below2-5). This
includes a conflicting one which show SII is not a biased agonist, but rather a distinct agonist of AT1R in a
G-protein-dependent manner by using a special experimental protocol 5). Biased agonists such as SII
continuously attract researchers studying RAS because the adverse effect of the parental peptide may be
avoided by using biased agonists specifically in the development of the therapeutic agents.
We now are distributing SII as one of our catalog items. In addition, we can also assist in the development of
a novel biased agonist of angiotensin II by synthesizing the candidate peptide(s) as custom service product(s),even under GMP guidelines.
1) H. Wei, S. Ahn, S.K. Shenoy, S.S. Karnik, L. Hunyady, L.M. Luttrell, and R.J. Lefkowitz, Proc. Natl. Acad. Sci. U.S.A.,
100, 10782 (2003). (Pharmacol.)2) C.M. Godin and S.S.G. Ferguson, Mini Rev. Med. Chem., 12, 812 (2012). (Review)3) R.T. Kendall, E.G. Strungs, S.M. Rachidi, M.-H. Lee, H.M. El-Shewy, D.K. Luttrell, M.G. Janech, and L.M. Luttrell,
J. Biol. Chem., 286, 19880 (2011). (Pharmacol.)4) P.C. Wilson, M.-H. Lee, K.M. Appleton, H.M. El-Shewy, T.A. Morinelli, Y.K. Peterson, L.M. Luttrell, and A.A. Jaffa,
J. Biol. Chem., 288, 18872 (2013). (Pharmacol.)5) A. Saulie｀re, M. Bellot, H. Paris, C. Denis, F. Finana, J.T. Hansen, M.-F. Altié, M.-H. Seguelas, A. Pathak, J.L. Hansen,
J.-M. Sénard, and C. Galés, Nat. Chem. Biol., 8, 622 (2012). (Pharmacol.)–5 –Apelin
Code

Compound4478-sApelin-36 (Human, 1-16 Amide)
SCNH2 (Selective Apelin-36 Cutting and Amidation Peptide)(Human, Simian, Canine)
Leu-Val-Gln-Pro-Arg-Gly-Ser-Arg-Asn-GlyPro-Gly-Pro-Trp-Gln-Gly-NH2

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(M.W. 1704.9) C74H117N27O20
Purity ≧99.0% (HPLC)

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0.1 mg

5,000[1241836-78-1]

Novel Apelinergic Family Member
When looking at the primary structure of human apelin-36 (Code 4362-s), there are several possible
processing sites to produce alternative peptides. Actually, [Pyr1]-apelin-13 (Code 4361-v) with its multiple
biological functions is generated from apelin-36. Both the parental apelin-36 and the processed 13-residue
peptide are considered to be a ligand for the APJ-receptor1).
Another processed peptide, Apelin-36 (Human, 1-16 Amide), abbreviated as SCNH2 (selective apelin-36
cutting and amidation peptide), was hypothesized, based on the presence of the amidation motif of Gly-ArgArg-Lys in apelin-36 and in fact, in early 2013 SCNH2 was identified as an endogenous peptide2). SCNH2
shows the similar functions to [Pyr1]-apelin-13: i) mitogenic activity at nM range, ii) augmentation ofangiogenesis (pM-nM), and iii) cell migration and invasion (pM). However, potencies of these activities arehigher in SCNH2 than those of not only [Pyr1]-apelin-13, but also vascular endothelial growth factor-A.
Furthermore, the receptor involved in the activity of SCNH2 is a pertussis toxin-resistant/chloral toxin-sensitive
G protein-coupled receptor (GPCR), indicating that the SCNH2 receptor is distinct from the APJ GPCR of [Pyr1]apelin-13 and apelin-36. Immunohistochemical staining reveals that endogenous SCNH2 is expressed inhuman placenta, lung and solid tumor tissue arrays. This novel peptide SCNH2 may be an essential member inthe study in the apelinergic system.
1) K. Tatemoto, M. Hosoya, Y. Habata, R. Fujii, T. Kakegawa, M.X. Zou, Y. Kawamata, S. Fukusumi, S. Hinuma,
C. Kitada, T. Kurokawa, H. Onda, and M. Fujino, Biochem. Biophys. Res. Commun., 251, 471 (1998).
(Apelin and APJ Receptor)
2) C. Fang, I. Avis, C. Bianco, N. Held, J. Morris, K. Ylaya, S.M. Hewitt, A.C. Aplin, R.F. Nicosia, L.A. Fung, J.D. Lewis,
W.G. Stetler-Stevenson, D.S. Salomon, and F. Cuttitta, Open J. Clin. Diagn., 3, 37 (2013). (Original & Pharmacol.)–6 –Catestatin
Code

Compound4470-vCatestatin (Human)
Chromogranin A (Human, 352-372)
Ser-Ser-Met-Lys-Leu-Ser-Phe-Arg-Ala-ArgAla-Tyr-Gly-Phe-Arg-Gly-Pro-Gly-Pro-GlnLeu

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0.5 mg16,000(M.W. 2326.7) C104H164N32O27S [197151-46-5]
Purity ≧99.0% including Met (O) analog (≦1.0%) (HPLC)

Antimicrobial Peptide / Regulator of Blood Pressure/Cardiac Function
In the primary structure of chromogranin A, a member of the granin family protein, many biologically active
peptides are encoded. Among others including chromogranin A (Human, 286-301 Amide) [Code 4214-v],
catestatin (human) is one of such endogenously processed peptides: catestatin (human) is composed of 21
amino acid residues corresponding to (352-372) of mother protein1). Nowadays, catestatin (human) is
categorized as a multifunctional peptide although this peptide was originally discovered to be an antagonist
against catecholamine secretion2-4). These functions include: i) stimulation of histamine release from mast cells,ii) induction of chemotaxis in human monocytes, iii) antimicrobial activity against skin pathogens, and iv)
cardiovascular function such as vasodilation and blood lowering effect.
Catestatin (human) is not the newly identified peptide, but may attract many researchers because review articles have been appeared frequently within several years.
1) D.S. Konecki, U.M. Benedum, H.-H. Gerdes, and W.B. Huttner, J. Biol. Chem., 262, 17026 (1987).
(Original; Chromogranin A cDNA)
2) J. Briolat, S.D. Wu, S.K. Mahata, B. Gonthier, D. Bagnard, S. Chasserot-Golaz, K.B. Helle, D. Aunis,
and M.H. Metz-Boutigue, Cell. Mol. Life Sci., 62, 377 (2005). (Review)3) B.S. Sahu, P.J. Sonawane, and N.R. Mahapatra, Cell. Mol. Life Sci., 67, 861 (2010). (Review)4) S.K. Mahata, M. Mahata, M.M. Fung, and D.T. O'Connor, Regul. Pept., 162, 33 (2010). (Review)–7 –TIP39Code

Compound4479-s

TIP39
Tuberoinfundibular Peptide of 39 Residues(Human, Bovine)
Ser-Leu-Ala-Leu-Ala-Asp-Asp-Ala-Ala-PheArg-Glu-Arg-Ala-Arg-Leu-Leu-Ala-Ala-LeuGlu-Arg-Arg-His-Trp-Leu-Asn-Ser-Tyr-MetHis-Lys-Leu-Leu-Val-Leu-Asp-Ala-Pro

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0.1 mg22,000(M.W. 4504.2) C202H325N61O54S [277302-47-3]
Purity ≧99.0% including Met(O) analog (≦1.0%) (HPLC)

Ligand for Parathyroid Hormone 2 Receptor
There are two G-protein-coupled receptors for parathyroid hormone (PTH): PTH 1 receptor (PTH1R) andPTH2R. Parathyroid Hormone (Human, 1-84) [Code 4134-v] is known to exert its biological activities throughPTH1R and PTH2R in human, while TIP39 (Tuberoinfundibular Peptide of 39 Residues) is the primary ligand
for the PTH2R.
TIP39 was first isolated from the bovine hypothalamus; later the primary structure of human TIP39 was
determined to be identical to that of bovine peptide by analyzing genomic DNA1). This particular ligandreceptor pair, TIP39-PTH2R, is localized in the brain and affords many regulatory effects on stress response,
hormone release such as Arg-vasopressin, GH and prolactin, anxiety and development of fear, regulation ofbody temperature, and nociceptive function, among others2-4). Considering this plethora of activities, TIP39
may be useful in the study to clarify the mechanism of neuroendocrine disorders and related diseases.
1) M.R. John, M. Arai, D.A. Rubin, K.B. Jonsson, and H. Ju
ppner, Endocrinology, 143, 1047 (2002). (Original)
2) L. Coutellier and T.B. Usdin, Behav. Brain Res., 222, 265 (2011). (Pharmacol.)3) E.L. Dimitrov, J. Kuo, K. Kohno, and T.B. Usdin, Proc. Natl. Acad. Sci. U.S.A., 110, 13156 (2013). (Pharmacol.)4) A. Dobolyi, M. Palkovits, and T.B. Usdin, Prog. Neurobiol., 90, 29 (2010). (Review)–8 –Phytosulfokine
CodeCompound4477-sPhytosulfokine
PSK(Plant, Asparagus officinalis L.)

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0.1 mg5,000(Ammonium Form)

Tyr(SO3H)-Ile-Tyr(SO3H)-Thr-Gln(M.W. 846.88) C33H46N6O16S2
Purity ≧99.0% (HPLC)[179667-62-0]

Potent Mitogenic Factor in Plants
O-sulfation of Tyr is an example of a posttranslational modification present in peptides and proteins, bywhich the modified molecule elicits the intrinsic biological function. In the animal kingdom, CCK-octapeptide(26-33) (sulfated form) [Code 4100-v], CCK-33 (human) [Code 4201-s], CCK-33 (porcine) [Code 4176-s] arewell-known examples of the sulfated-Tyr-containing peptide. The same is true in higher plants: phytosulfokine(PSK) was identified in the culture medium of Asparagus officinalis by Matsubayashi and Sakagami in 19961).
PSK is a 5-residue peptide that the Tyr residues at positions 1 and 3 are sulfated. Later, the same peptide was
identified in other plants including rice and carrots; therefore PSK is recognized as being a widely distributed
peptide in plants.
Functionally, PSK is considered to be a plant hormone because PSK stimulates: i) plant cell proliferation anddifferentiation at 3.8 nM (ED50), ii) chlorophyll synthesis, iii) adventitious root and bud formation, iv) somatic
embryogenesis, and v) attenuation of pattern-triggered immunity (TPI)2-5). These activities are mediated by
specific PSK receptor(s)6,7).
This posttranslationally modified peptide hormone PSK is convincingly indispensable in research to clarify
physiological functions in plants.
1) Y. Matsubayashi and Y. Sakagami, Proc. Natl. Acad. Sci. U.S.A., 93, 7623 (1996). (Original: Structure & Pharmacol.)2) Y. Matsubayashi, H. Shinohara, and M. Ogawa, Chem. Rec., 6, 356 (2006).
(Review; Structure-Activiry Relationship & Receptor-Ligand Interaction)3) A. Bahyrycz and D. Konopińska, J. Pept. Sci., 13, 787 (2007). (Review; Pharmacol.)4) D. Igarashi, K. Tsuda, and F. Katagiri, Plant J., 71, 194 (2012). (Pharmacol.)5) N. Stu
hrwohldt, R.I. Dahlke, B. Steffens, A. Johnson, and M. Sauter, PLoS One, 6, e21054 (2011). (Pharmacol.)6) Y. Matsubayashi, M. Ogawa, A. Morita, and Y. Sakagami, Science, 296, 1470 (2002). (Specific Receptor)
7) Y. Matsubayashi, J. Cell Sci., 116, 3863 (2003). (Review; Specific Receptor)–9 –Peptide Tool
Code

Compound3406-v

Amyloid β-Protein (1-42, O-acyl isopeptide)
26-O-acyl isoAβ1-42-20

(Trifluoroacetate Form)(1-25) : Asp-Ala-Glu-Phe-Arg-His-Asp-Ser-Gly-TyrGlu-Val-His-His-Gln-Lys-Leu-Val-Phe-PheAla-Glu-Asp-Val-Gly(26-42) : Ser-Asn-Lys-Gly-Ala-Ile-Ile-Gly-Leu-MetVal-Gly-Gly-Val-Val-Ile-Ala(Ester bond between Gly25 α-carboxyl group and Ser26 β-hydroxyl group)New(M.W. 4514.0) C203H311N55O60S
Purity ≧95.0% (HPLC)

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0.5 mg30,000[753459-14-2]

H 2N

pH Click Peptide for Amyloid β -Protein (Human, 1-42)
Amyloid β-protein (1-42, O-acyl isopeptide) is an artificial peptide designed by Professor Kiso's group1,2).
The structural feature of this peptide is an ester linkage, instead of the native carboxamide, between Gly25 andSer26, rendering this a branched peptide at Ser26 and now feasible to dissolve in water. The ester bond from theside chain of Ser26 is reported to be stable at pH 2.0, but easily and efficiently converted to the carboxamidebond by O-to-N acyl migration under the basic conditions such as pH 7.4. The nascent amyloid β-protein(1-42) initiates the conformational change from a random coil to a β-structure, initiating aggregation1-3).
Our synthesis group has recently succeeded in synthesizing the amyloid β-protein (1-42, O-acyl isopeptide)by Boc chemistry using a novel isoacyl-dipeptide unit in collaboration with Professor Kiso4). We are very
pleased to offer this as a "Peptide Tools" catalog item, giving customers further flexibility in their Alzheimer's
disease research.
Amyloid β-Protein (1-42, O-acyl isopeptide)[Trifluoroacetate Form]
O-to-N Acyl Migration at pH 7.4

Structure: Random Coil at pH 2.0

Amyloid β-Protein (1-42)
Structure Change:
Random Coil to β-Structure1) Y. Sohma, M. Sasaki, Y. Hayashi, T. Kimura, and Y. Kiso, Tetrahedron Lett., 45, 5965 (2004).
(Original; Chem. Synthesis)2) A.Taniguchi, Y. Sohma, Y. Hirayama, H. Mukai, T. Kimura, Y. Hayashi, K. Matsuzaki, and Y. Kiso, ChemBioChem,
10, 710 (2009).
3) R. Roychaudhuri, A. Lomakin, S. Bernstein, X. Zheng, M.M. Condron, G.B. Benedek, M. Bowers, and D.B. Teplow,
J. Mol. Biol., 426, 2422 (2014).
4) a) T. Yoshiya, T. Uemura, T. Maruno, S. Kubo, Y. Kiso, Y. Sohma, Y. Kobayashi, K. Yoshizawa-Kumagaye,
and Y. Nishiuchi, J. Pept. Sci., 20, 669 (2014); b) T. Yoshiya, T. Maruno, T. Uemura, S. Kubo, Y. Kiso, Y. Sohma,
K. Yoshizawa-Kumagaye,Y. Kobayashi, and Y. Nishiuchi, Bioorg. Med. Chem. Lett., 24, 3861 (2014).

Note: We have not described the conformational characteristics of amyloid β-protein (1-42) (Code 4349-v) in
our catalog. However, we actually offered all of the already shipped vials and will offer the new lot vials
henceforth after confirming the conformational change in CD spectra; from a random coil to a β-structure inaqueous buffer at pH 7.4 and 37 ℃ within 24 h at the peptide concentration of 10 μM. This is also applicable
to amyloid β-protein (1-43) (Code 4370-v).

– 10 –

Enzyme Substrate
Code

Compound3233-v

Nma-Phe-His-Lys(Dnp)

New

-20

Price:Yen
Vial

1 mg

10,000(Trifluoroacetate Form)[2-(Methylamino)benzoyl]-L-phenylalanyl-L-histidylNε-(2,4-dinitrophenyl)-L-lysine(M.W. 729.74)

C35H39N9O9Purity ≧98.0% (HPLC)

Fluorescence-Quenching Substrate for Angiotensin I Converting Enzyme and Carboxypeptidase Y
1) S. Takahashi, H. Ono, T. Gotoh, K. Yoshizawa-Kumagaye, and T. Sugiyama, Biomed. Res., 32, 407 (2011).

Fmoc-Amino Acids
Code

Compound2328

Fmoc-His(MBom)2～10

Nα-9-FluorenylmethoxycarbonylNπ-4-methoxybenzyloxymethyl-L-histidine

New(M.W. 527.57) C30H29N3O6
Purity ≧98.0% (HPLC)

Price:Yen
Bulk

1g
5g

10,00045,000[1327338-56-6]

1) H. Hibino and Y. Nishiuchi, Tetrahedron Lett., 52, 4947 (2011).
2) H. Hibino, Y. Miki, and Y. Nishiuchi, J. Pept. Sci., 18, 763 (2012).
3) K. Sakamoto, K. Sato, A. Shigenaga, K. Tsuji, S. Tsuda, H. Hibino, Y. Nishiuchi, and A. Otaka,
J. Org. Chem., 77, 6948 (2012).

2329

New

2～10

Bulk

Fmoc-Cys(Dpm)

5g

10,0009-Fluorenylmethoxycarbonyl-S-diphenylmethyl-L-cysteine(M.W. 509.62) C31H27NO4S
Purity ≧98.0% (HPLC)[247595-29-5]

1) M. Góngora-Ben́tez, L. Mendive-Tapia, I. Ramos-Tomillero, A.C. Breman, J. Tulla-Puche, and F. Albericio,
Org. Lett., 14, 5472 (2012).
2) H. Hibino, Y. Miki, and Y. Nishiuchi, J. Pept. Sci., 20, 30 (2014).

2330

New

2～10

Bulk

Fmoc-Cys(Ddm)

1g

10,0009-Fluorenylmethoxycarbonyl-S-4,4'-dimethoxydiphenylmethyl-L-cysteine(M.W. 569.67) C33H31NO6S
Purity ≧98.0% (HPLC)[1403825-56-8]

1) M. Góngora-Ben́tez, L. Mendive-Tapia, I. Ramos-Tomillero, A.C. Breman, J. Tulla-Puche, and F. Albericio,
Org. Lett., 14, 5472 (2012).
2) H. Hibino, Y. Miki, and Y. Nishiuchi, J. Pept. Sci., 20, 30 (2014).

– 11 –

笊

ご希望のペプチド（Cys 含有ペプチドも含む）
2-200 残基（200 残基を越える場合も可能です。ご相談下さい）

笆
笳
笘
笙
笞
笵
笨
笶
筐
筺

生理活性ペプチドとその誘導体
細胞膜透過性ペプチド（Tat, オリゴアルギニン , Penetratin など）
各種酵素基質（MCA, AFC, p NA, その他の蛍光，発色基質など）
消光性蛍光基質（Nma-Dnp，MOCAc-Dnp，Dabcyl-EDANS の組合せなど）
酵素阻害剤（アルデヒド，フルオロメチルケトン，クロロメチルケトン，ボロン酸誘導体など）
ジスルフィド結合含有ペプチド（1 組，2 組，3 組以上。分子内，分子間）
環状ペプチドおよび枝分かれペプチド
鎖状および環状デプシペプチド
リン酸化ペプチド［Ser（PO3H2），Thr（PO3H2），Tyr（PO3H2）誘導体］
ホスホノペプチド［リン酸化ペプチドのカルバ型誘導体］［Ser（PO3H2），Thr（PO3H2），Tyr（PO3H2）に対応するホスファターゼ抵抗性誘導体］

笄筍

硫酸化ペプチド［Tyr（SO3H）］
アミノ基修飾誘導体（Biotinyl 化 , Myristoyl 化 , Palmitoyl 化 , Methyl 化 , Malonyl 化 , PEG 化 ,Acetyl 化 , Boc 化 , Z 化 , など種々の修飾）笋筌筅

チオール基修飾誘導体（Farnesyl 化，Geranyl 化，Biotinyl 化など）
蛍光標識ペプチド（FITC, Rhodamine, BODIPY, DY- シリーズなど 380 nm-730 nm に対応）
糖ペプチド［Asn（GlcNAc）, Ser/Thr（GalNAc）, Ser/Thr（Gal-GalNAc）, Ser/Thr（Neu-Gal-GalNAc）,
Ser/Thr（GlcNAc）, 1-Deoxyfructosyl 含有ペプチドなど］

筵
筥
筴
筧
筰
筱
筬
筮

非天然アミノ酸含有ペプチド（ハイプシン , システインスルフィン酸

他多数）

ペプチド結合の修飾（還元型、スタチン型など）
アミノ酸誘導体 , 保護ペプチド
安定同位体ラベルアミノ酸含有ペプチド（13C，15N，2H など）
ペプチドアルコール
糖関連化合物（ガングリオシド , Lipid A, 糖ヌクレオチドなど）
一般有機化合物
その他

受託合成量： 標準 10mg 〜 25mg から g、kg オーダーまで承ります。（お見積り依頼の際に、ご相談下さい）
納期： 固相法にて合成可能な通常のペプチド 25mg の場合：通常 2-4 週間
液相法などその他の方法で合成する場合はご相談させていただきます。

保 証 純 度： 通常、トリフルオロ酢酸塩でご提供いたします。他の塩をご希望の場合はご相談下さい。
規格 （1）逆相 HPLC で検定：90％以上（精製品）（2）逆相 HPLC で検定：95% 以上（精製品）（3）逆相 HPLC で検定：99% 以上（精製品）
通常、HPLC チャート、アミノ酸分析結果、質量分析結果を添付いたします。
その他の分析項目につきましてはご相談させていただきます。
価格： 個別にお見積りいたしますので、弊社 Web Site から、あるいは E-mail、Fax にてご相談下さい。

` 医薬品開発研究用カスタム合成
弊社は、医薬品製造業許可を取得しており、医薬品原薬および原薬中間体の製造が可能です。
GMP 対応、治験薬 GMP 対応など個別にご相談させていただきます。

 12 

ペプチド合成依頼書（□見積依頼書

□発注）
年

月

日

ご依頼者
ご 住 所〒□□□-□□□□

勤 務 先

ご所属

フ リ ガ ナ

お 名 前L

--F A X

-

-

T

E

（内線）

E - m a i l
アミノ酸配列（アミノ酸配列は1文字表記、3文字表記どちらでも結構です）

N末端
1

C末端→
2

3

ペプチド量
純

4

5

6

7

8

9

□ 25 mg(標準量)

10

11

13

14

□ 50 mg □度 (逆相HPLC)□ 90%以上保証(精製品)

ご用途

12

□ 抗原(抗体作製)用

15

16

17

mg □

18

19

g □

20

kg

□ 95%以上保証(精製品)□ その他（コンジュゲーション・抗体作製）

お差し仕えなければご記入下さい。

コンジュゲーション □ 希望する □ 希望しない
希望結合部位□ N端

キャリアー蛋白質の種類 □ BSA
抗体作製(ウサギ)

□ C端□ その他()□ KLH □ OVA □ その他()

□ 希望する（羽）□ 希望しない

抗体アフィニティー精製 □ 希望する □ 希望しない担体への結合□ ペプチド □ その他(

抗体の標識

□ ビオチン標識)□ パーオキシダーゼ標識（過ヨウ素酸法）

備考 (ご要望事項など)

お願いお見積り依頼・ご発注は、アミノ酸配列確認のため、FAXやE-mailなどの文書でお願いいたします。

株式会社

ペプチド研究所〒567-0085 大阪府 茨木市 彩都 あさぎ 7-2-9
電話072-643-4343 (直通) FAX072-643-4422
E-mail: custom＠peptide.co.jp http://www.peptide.co.jp/