Efficient synthesis of polypeptide‐α‐thioester by the method combining polypeptide expression and chemical activation for the semi‐synthesis of interferon‐γ having oligosaccharides | Zendy

Kajihara Yasuhiro | Zendy; Kanemitsu Yurie | Zendy; Nishihara Mika | Zendy; Okamoto Ryo | Zendy; Izumi Masayuki | Zendy

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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.

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