Synthesis of a Glycopeptide Containing Oligosaccharides: Chemoenzymatic Synthesis of Eel Calcitonin Analogues Having Natural N-Linked Oligosaccharides

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• 作者：Mamoru Mizuno ; Katsuji Haneda ; Reiko Iguchi ; Ikuyo Muramoto ; Toru Kawakami ; Saburo Aimoto ; Kenji Yamamoto ; and Toshiyuki Inazu
• 刊名：Journal of the American Chemical Society
• 出版年：1999
• 出版时间：January 20, 1999
• 年：1999
• 卷：121
• 期：2
• 页码：284 - 290
• 全文大小：118K
• 年卷期：v.121,no.2(January 20, 1999)
• ISSN：1520-5126

文摘

We describe a novel chemoenzymatic synthesis of eel calcitonin (eCT) glycopeptide analogues havingnatural N-linked oligosaccharides, such as a disialo biantennary complex-type [(NeuAc-Gal-GlcNAc-Man)₂-Man-GlcNAc₂], an asialo complex-type [(Gal-GlcNAc-Man)₂-Man-GlcNAc₂], and a high-mannose type [Man₆-GlcNAc₂] as model compounds for glycoprotein synthesis. First, a glycoprotein containing N-acetylglucosamine(GlcNAc) was prepared by a chemical synthesis. Next, natural oligosaccharides were added to the preparedglycopeptide containing GlcNAc by a transglycosylation reaction using endo--N-acetylglucosaminidase (endo--GlcNAc-ase) from Mucor hiemalis.