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

J Appl Glycosci (1999). 2020 Nov 20;67(4):129-135. doi: 10.5458/jag.jag.JAG-2020_0009. eCollection 2020.

Abstract

Utilizing transglycosylation reaction catalyzed by β- N -acetylhexosaminidase of Stenotrophomonas maltophilia , β-D-fructofuranosyl-(2↔1)-α- N , N ´diacetylchitobioside (GlcNAc 2 -Fru) was synthesized from N -acetylsucrosamine and N , N ´-diacetylchitobiose (GlcNAc 2 ), and β-D-fructofuranosyl-(2↔1)-α- N , N ´, N ´´-triacetylchitotrioside (GlcNAc 3 -Fru) was synthesized from GlcNAc 2 -Fru and GlcNAc 2 . Through purification by charcoal column chromatography, pure GlcNAc 2 -Fru and GlcNAc 3 -Fru were obtained in molar yields of 33.0 % and 11.7 % from GlcNAc 2 , 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.

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