The application of an aryl hydrazine linker prevents ß‐elimination side products in the SPPS of  C ‐terminal cysteine peptides | Zendy

Ni Shuaijian | Zendy; Zhang Huibin | Zendy; Huang Wenlong | Zendy; Zhou Jinpei | Zendy; Qian Hai | Zendy; Chen Wei | Zendy

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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.

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