Enzymatic Synthesis and Structural Confirmation of Novel Oligosaccharide, D-Fructofuranose-linked Chitin Oligosaccharide

Hiroki Hosaka; Sayaka Shirai; Sora Fujita; Mitsuru Tashiro; Takako Hirano; Wataru Hakamata; Toshiyuki Nishio

doi:10.5458/jag.jag.JAG-2020_0009

Note

Enzymatic Synthesis and Structural Confirmation of Novel Oligosaccharide, D-Fructofuranose-linked Chitin Oligosaccharide

Hiroki Hosaka, Sayaka Shirai, Sora Fujita, Mitsuru Tashiro, Takako Hirano, Wataru Hakamata, Toshiyuki Nishio

Author information

Hiroki Hosaka
Bioresource Utilization Science Course, Graduate School of Bioresource Sciences, Nihon University
Sayaka Shirai
Bioresource Utilization Science Course, Graduate School of Bioresource Sciences, Nihon University
Sora Fujita
Bioresource Utilization Science Course, Graduate School of Bioresource Sciences, Nihon University
Mitsuru Tashiro
Department of Chemistry, College of Science and technology, Meisei University
Takako Hirano
Bioresource Utilization Science Course, Graduate School of Bioresource Sciences, Nihon University
Department of Chemistry and Life Science, College of Bioresource Sciences, Nihon University
Wataru Hakamata
Bioresource Utilization Science Course, Graduate School of Bioresource Sciences, Nihon University
Department of Chemistry and Life Science, College of Bioresource Sciences, Nihon University
Toshiyuki Nishio
Bioresource Utilization Science Course, Graduate School of Bioresource Sciences, Nihon University
Department of Chemistry and Life Science, College of Bioresource Sciences, Nihon University

Keywords: noble oligosaccharide, D-fructofuranose-linked chitin oligosaccharides, enzymatic synthesis, β-N-acetylhexosaminidase, structural confirmation

JOURNAL OPEN ACCESS FULL-TEXT HTML

2020 Volume 67 Issue 4 Pages 129-135

DOI https://doi.org/10.5458/jag.jag.JAG-2020_0009

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Abstract

Utilizing transglycosylation reaction catalyzed by β-N-acetylhexosaminidase of Stenotrophomonas maltophilia, β-D-fructofuranosyl-(2↔1)-α-N, N´diacetylchitobioside (GlcNAc₂-Fru) was synthesized from N-acetylsucrosamine and N, N´-diacetylchitobiose (GlcNAc₂), and β-D-fructofuranosyl-(2↔1)-α-N, N´, N´´-triacetylchitotrioside (GlcNAc₃-Fru) was synthesized from GlcNAc₂-Fru and GlcNAc₂. Through purification by charcoal column chromatography, pure GlcNAc₂-Fru and GlcNAc₃-Fru were obtained in molar yields of 33.0 % and 11.7 % from GlcNAc₂, respectively. The structures of these oligosaccharides were confirmed by comparing instrumental analysis data of fragments obtained by enzymatic hydrolysis and acid hydrolysis of them with known data of these fragments.

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