Efficient synthesis of polypeptide-α-thioester by the method combining polypeptide expression and chemical activation for the semi-synthesis of interferon-γ having oligosaccharides.
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-His6 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 NaNO2 /acid conditions followed by thiolysis in 83% yield.
Department of chemistry, Osaka University, 1-1, Machikaneyama, Toyonaka, 560-0043, Japan.
Yasuhiro
Y
Kajihara
Yurie
Y
Kanemitsu
Mika
M
Nishihara
Ryo
R
Okamoto
Masayuki
M
Izumi
D000595:Amino Acid Sequence; D002851:Chromatography, High Pressure Liquid; D004591:Electrophoresis, Polyacrylamide Gel; D004952:Esters / Q000737:chemistry*; D007371:Interferon-gamma / Q000138:chemical synthesis* / Q000737:chemistry; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000737:chemistry*; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D017386:Sequence Homology, Amino Acid; D021241:Spectrometry, Mass, Electrospray Ionization; D013438:Sulfhydryl Compounds / Q000737:chemistry*
D004952:Esters; D009844:Oligosaccharides; D010455:Peptides; D013438:Sulfhydryl Compounds; D007371:Interferon-gamma
chemical conversion; peptide expression; peptide-α-thioester; semi-synthesis