Aspartate racemization in synthetic peptides. Part 2. Tendency to racemization of aminosuccinyl residue

István Schön, Tamás Szirtes, Attila Rill, Gábor Balogh, Zsolt Vadász, J. Seprődi, István Teplán, Naoyoshi Chino, Kumiko Yoshizawa Kumogaye, Shumpei Sakakibara

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

Aminosuccinyl (Asu) peptides, containing a strained ring system, are very vulnerable to epimerization and, during their formation, even as transients, in the presence of nucleophilic and non-nucleophilic bases, partial epimerization occurs. In the presence of nucleophilic bases, Asu-peptides transform to a partially epimerized mixture of α- and β-aspartyl peptides, with the preponderance of the β- over the α-peptides. In the absence of any internal basic functionality such as the protonated guanidino group, chirally pure Asu-peptides could be synthesized by heating of β-benzyl-aspartyl [Asp(OBzl)] peptides in dimethylformamide to elevated temperatures or, from aspartyl (Asp) peptides having a free carboxy group, by the usual treatment with pentafluorophenol or 1-hydroxybenzotriazole-dicyclohexylcarbodiimide. However, in the presence of the strongly basic acetate ion and/or a guanidinium group the probability of aspartate racemization is increased.

Original languageEnglish
Pages (from-to)3213-3223
Number of pages11
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number12
Publication statusPublished - 1991

Fingerprint

Aspartic Acid
Peptides
Dicyclohexylcarbodiimide
Dimethylformamide
Guanidine
Acetates
Ions
Heating

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Aspartate racemization in synthetic peptides. Part 2. Tendency to racemization of aminosuccinyl residue. / Schön, István; Szirtes, Tamás; Rill, Attila; Balogh, Gábor; Vadász, Zsolt; Seprődi, J.; Teplán, István; Chino, Naoyoshi; Kumogaye, Kumiko Yoshizawa; Sakakibara, Shumpei.

In: Journal of the Chemical Society, Perkin Transactions 1, No. 12, 1991, p. 3213-3223.

Research output: Contribution to journalArticle

Schön, I, Szirtes, T, Rill, A, Balogh, G, Vadász, Z, Seprődi, J, Teplán, I, Chino, N, Kumogaye, KY & Sakakibara, S 1991, 'Aspartate racemization in synthetic peptides. Part 2. Tendency to racemization of aminosuccinyl residue', Journal of the Chemical Society, Perkin Transactions 1, no. 12, pp. 3213-3223.
Schön, István ; Szirtes, Tamás ; Rill, Attila ; Balogh, Gábor ; Vadász, Zsolt ; Seprődi, J. ; Teplán, István ; Chino, Naoyoshi ; Kumogaye, Kumiko Yoshizawa ; Sakakibara, Shumpei. / Aspartate racemization in synthetic peptides. Part 2. Tendency to racemization of aminosuccinyl residue. In: Journal of the Chemical Society, Perkin Transactions 1. 1991 ; No. 12. pp. 3213-3223.
@article{a52441e723c24a5b83c427c80f16e933,
title = "Aspartate racemization in synthetic peptides. Part 2. Tendency to racemization of aminosuccinyl residue",
abstract = "Aminosuccinyl (Asu) peptides, containing a strained ring system, are very vulnerable to epimerization and, during their formation, even as transients, in the presence of nucleophilic and non-nucleophilic bases, partial epimerization occurs. In the presence of nucleophilic bases, Asu-peptides transform to a partially epimerized mixture of α- and β-aspartyl peptides, with the preponderance of the β- over the α-peptides. In the absence of any internal basic functionality such as the protonated guanidino group, chirally pure Asu-peptides could be synthesized by heating of β-benzyl-aspartyl [Asp(OBzl)] peptides in dimethylformamide to elevated temperatures or, from aspartyl (Asp) peptides having a free carboxy group, by the usual treatment with pentafluorophenol or 1-hydroxybenzotriazole-dicyclohexylcarbodiimide. However, in the presence of the strongly basic acetate ion and/or a guanidinium group the probability of aspartate racemization is increased.",
author = "Istv{\'a}n Sch{\"o}n and Tam{\'a}s Szirtes and Attila Rill and G{\'a}bor Balogh and Zsolt Vad{\'a}sz and J. Seprődi and Istv{\'a}n Tepl{\'a}n and Naoyoshi Chino and Kumogaye, {Kumiko Yoshizawa} and Shumpei Sakakibara",
year = "1991",
language = "English",
pages = "3213--3223",
journal = "Journal of the Chemical Society, Perkin Transactions 1",
issn = "1472-7781",
publisher = "Chemical Society",
number = "12",

}

TY - JOUR

T1 - Aspartate racemization in synthetic peptides. Part 2. Tendency to racemization of aminosuccinyl residue

AU - Schön, István

AU - Szirtes, Tamás

AU - Rill, Attila

AU - Balogh, Gábor

AU - Vadász, Zsolt

AU - Seprődi, J.

AU - Teplán, István

AU - Chino, Naoyoshi

AU - Kumogaye, Kumiko Yoshizawa

AU - Sakakibara, Shumpei

PY - 1991

Y1 - 1991

N2 - Aminosuccinyl (Asu) peptides, containing a strained ring system, are very vulnerable to epimerization and, during their formation, even as transients, in the presence of nucleophilic and non-nucleophilic bases, partial epimerization occurs. In the presence of nucleophilic bases, Asu-peptides transform to a partially epimerized mixture of α- and β-aspartyl peptides, with the preponderance of the β- over the α-peptides. In the absence of any internal basic functionality such as the protonated guanidino group, chirally pure Asu-peptides could be synthesized by heating of β-benzyl-aspartyl [Asp(OBzl)] peptides in dimethylformamide to elevated temperatures or, from aspartyl (Asp) peptides having a free carboxy group, by the usual treatment with pentafluorophenol or 1-hydroxybenzotriazole-dicyclohexylcarbodiimide. However, in the presence of the strongly basic acetate ion and/or a guanidinium group the probability of aspartate racemization is increased.

AB - Aminosuccinyl (Asu) peptides, containing a strained ring system, are very vulnerable to epimerization and, during their formation, even as transients, in the presence of nucleophilic and non-nucleophilic bases, partial epimerization occurs. In the presence of nucleophilic bases, Asu-peptides transform to a partially epimerized mixture of α- and β-aspartyl peptides, with the preponderance of the β- over the α-peptides. In the absence of any internal basic functionality such as the protonated guanidino group, chirally pure Asu-peptides could be synthesized by heating of β-benzyl-aspartyl [Asp(OBzl)] peptides in dimethylformamide to elevated temperatures or, from aspartyl (Asp) peptides having a free carboxy group, by the usual treatment with pentafluorophenol or 1-hydroxybenzotriazole-dicyclohexylcarbodiimide. However, in the presence of the strongly basic acetate ion and/or a guanidinium group the probability of aspartate racemization is increased.

UR - http://www.scopus.com/inward/record.url?scp=37049081620&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=37049081620&partnerID=8YFLogxK

M3 - Article

AN - SCOPUS:37049081620

SP - 3213

EP - 3223

JO - Journal of the Chemical Society, Perkin Transactions 1

JF - Journal of the Chemical Society, Perkin Transactions 1

SN - 1472-7781

IS - 12

ER -