A dimethoxytriazine type glycosyl donor enables a facile chemo-enzymatic route toward α-linked N-acetylglucosaminyl-galactose disaccharide unit from gastric mucin

Masato Noguchi; Miwa Nakamura; Ayaka Ohno; Tomonari Tanaka; Atsushi Kobayashi; Masaki Ishihara; Masaya Fujita; Akiko Tsuchida; Mamoru Mizuno; Shin-ichiro Shoda

doi:10.1039/C2CC30946G

A dimethoxytriazine type glycosyl donor enables a facile chemo-enzymatic route toward α-linked N-acetylglucosaminyl-galactose disaccharide unit from gastric mucin†

Masato Noguchi,^a Miwa Nakamura,^a Ayaka Ohno,^a Tomonari Tanaka,^b Atsushi Kobayashi,^a Masaki Ishihara,^a Masaya Fujita,^c Akiko Tsuchida,^c Mamoru Mizuno^c and Shin-ichiro Shoda*^a

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^a Department of Biomolecular Engineering, Tohoku University, 6-6-11-514 Aoba, Aoba-ku, Sendai 980-8579, Japan
E-mail: shoda@poly.che.tohoku.ac.jp
Fax: +81-22-795-7293
Tel: +81-22-795-7230

^b Department of Biobased Materials Science, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto 606-8585, Japan

^c The Noguchi Institute, 1-8-1 Kaga, Itabashi-ku, Tokyo 173-0003, Japan

Abstract

An efficient chemo-enzymatic process for construction of the α-linked disaccharide unit (GlcNAcα1-4Gal) found in gastric mucin has been developed. The process consists of a one-step preparation of a novel triazine type glycosyl donor in water and the subsequent transglycosylation to a galactose derivative catalysed by α-N-acetylglucosaminidase.

Chemical Communications

A dimethoxytriazine type glycosyl donor enables a facile chemo-enzymatic route toward α-linked N-acetylglucosaminyl-galactose disaccharide unit from gastric mucin†

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A dimethoxytriazine type glycosyl donor enables a facile chemo-enzymatic route toward α-linked N-acetylglucosaminyl-galactose disaccharide unit from gastric mucin

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