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The application of an aryl hydrazine linker prevents ß‐elimination side products in the SPPS of C ‐terminal cysteine peptides
Author(s) -
Ni Shuaijian,
Zhang Huibin,
Huang Wenlong,
Zhou Jinpei,
Qian Hai,
Chen Wei
Publication year - 2010
Publication title -
journal of peptide science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 66
eISSN - 1099-1387
pISSN - 1075-2617
DOI - 10.1002/psc.1240
Subject(s) - linker , cysteine , chemistry , solid phase synthesis , hydrazine (antidepressant) , peptide , amino acid , yield (engineering) , peptide synthesis , combinatorial chemistry , side chain , alanine , aryl , stereochemistry , organic chemistry , biochemistry , enzyme , metallurgy , operating system , materials science , polymer , alkyl , computer science
Solid‐phase synthesis allows for the preparation of some complex cysteine‐containing peptides with both a high yield and purity. However, side reactions during chain elongation such as modification of amino acid residues have been found in C ‐terminal cysteine peptides. We identified 3‐(1‐piperidinyl)‐alanine peptides, corroborated the mechanism of the side reaction, and introduced an efficient approach for the Fmoc‐based synthesis of C ‐terminal cysteine peptides using an aryl hydrazine linker. Copyright © 2010 European Peptide Society and John Wiley & Sons, Ltd.