Synthesis of Oligopeptides Through O-acyl Isopeptide Method

Title: Synthesis of Oligopeptides Through O-acyl Isopeptide Method

Volume: 18 Issue: 8

Author(s): H. S. Lalithamba, H. P. Hemantha and Vommina V. Sureshbabu

Affiliation:

Keywords: O-acyl isopeptide, ‘click’ peptide, O→N intramolecular acyl migration, Hydrogen bonding, pseudoproline moiety, depsi peptide, polarity, oligopeptide fragments, HPLC chromatogra, anticancer prodrugs, hassle-free peptide assembly, click peptide method, switch peptide, anhydride method, isopeptide, depsi linkage, Amino acidsO-acyl isopeptide, ‘click’ peptide, O→N intramolecular acyl migration, Hydrogen bonding, pseudoproline moiety, depsi peptide, polarity, oligopeptide fragments, HPLC chromatogra, anticancer prodrugs, hassle-free peptide assembly, click peptide method, switch peptide, anhydride method, isopeptide, depsi linkage, Amino acids

Abstract: The O-acyl isopeptide method has recently gained attention as an efficient protocol for the synthesis of ‘difficult sequence‘ peptides. Herein, synthesis of three oligopeptides of different length, a pentapeptide Gly-Leu-Leu-Ser-Val, a heptapeptide fragment 285-291 of transmembrane (M7-24-T40) Ala-Val-Leu-Ser-Leu-Pro-Leu and a decapeptide, Gly- Leu-Leu-Ser-Val-Leu-Gly-Ser-Val-Ala were demonstrated in solution phase by employing O-acyl isopeptide method. The peptides were established through an efficient pH triggered intramolecular O→N acyl migration under physiological conditions. The reactions were clean and complete in appreciable length of time.

Cite this article as:

S. Lalithamba H., P. Hemantha H. and V. Sureshbabu Vommina, Synthesis of Oligopeptides Through O-acyl Isopeptide Method, Protein & Peptide Letters 2011; 18 (8) . https://dx.doi.org/10.2174/092986611795713961