Studies on epimerization-free methods for the preparation of aminosuccinyl peptides

Zsolt Vadasz, J. Seprődi, Istvan Teplan

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

We have found that guanidine acetate catalyses the transformation of a β-benzyl-aspartyl peptide (Boc-Asp-(OBzl)-Leu-Trp-OMe) to an aminosuccinyl peptide (Boc-Asu-Leu-Trp-OMe). The reaction was accompanied by partial epimerization. However, not even a small amount of epimerization could be detected when the aminosuccinyl peptide was synthesised from Boc-Asp-Leu-Trp-OMe with the addition of DIC, HOPfp and guanidine acetate (as a catalyst). This reaction seems to be suitable for the epimerization-free solid phase synthesis of aminosuccinyl peptides, e.g. Asu6-Lamprey-III-GnRH (Glp-His-Trp-Ser-His-Asu-Trp-Lys-Pro-Gly-NH2).

Original languageEnglish
Pages (from-to)339-344
Number of pages6
JournalLetters in Peptide Science
Volume2
Issue number6
DOIs
Publication statusPublished - Feb 1996

Fingerprint

Peptides
Guanidine
Acetates
Dacarbazine
Solid-Phase Synthesis Techniques
Catalysts
tert-butyloxycarbonyl-tryptophyl-leucyl-asparagine
t-butyloxycarbonylaspartic acid alpha-benzyl ester
gonadotropin-releasing hormone-III

Keywords

  • Aminosuccinimide
  • Peptide synthesis
  • Racemization

ASJC Scopus subject areas

  • Biochemistry

Cite this

Studies on epimerization-free methods for the preparation of aminosuccinyl peptides. / Vadasz, Zsolt; Seprődi, J.; Teplan, Istvan.

In: Letters in Peptide Science, Vol. 2, No. 6, 02.1996, p. 339-344.

Research output: Contribution to journalArticle

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