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Efficient synthesis of polypeptide‐α‐thioester by the method combining polypeptide expression and chemical activation for the semi‐synthesis of interferon‐γ having oligosaccharides
Author(s) -
Kajihara Yasuhiro,
Kanemitsu Yurie,
Nishihara Mika,
Okamoto Ryo,
Izumi Masayuki
Publication year - 2014
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.2709
Subject(s) - thioester , hydrazide , chemistry , yield (engineering) , biochemistry , oligosaccharide , native chemical ligation , chemical synthesis , stereochemistry , combinatorial chemistry , in vitro , organic chemistry , enzyme , materials science , metallurgy
In order to synthesize interferon‐γ glycoform having an oligosaccharide at the 97 position by a semi‐synthetic method, interferon‐γ‐polypeptide‐(1–94)‐α‐hydrazide was prepared by the specific Cys‐cyanylation of polypeptide‐(1–94)‐Cys‐His 6 expressed from E. coli and subsequent hydrazinolysis in 22% yield (two steps). This polypeptide‐α‐hydrazide was then converted into corresponding polypeptide‐α‐thioester under NaNO 2 /acid conditions followed by thiolysis in 83% yield. Copyright © 2014 European Peptide Society and John Wiley & Sons, Ltd.