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Synthesis of Oligopeptides Through O-acyl Isopeptide Method

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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.

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

Document Type: Research Article

Publication date: 2011-08-01

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  • Protein & Peptide Letters publishes short papers in all important aspects of protein and peptide research, including structural studies, recombinant expression, function, synthesis, enzymology, immunology, molecular modeling, drug design etc. Manuscripts must have a significant element of novelty, timeliness and urgency that merit rapid publication. Reports of crystallisation, and preliminary structure determinations of biologically important proteins are acceptable. Purely theoretical papers are also acceptable provided they provide new insight into the principles of protein/peptide structure and function.
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