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Current Organic Chemistry


ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

Research Article

Thermostable α-Glucan Phosphorylase-catalyzed Enzymatic Chain-elongation to Produce 6-Deoxygenated α(1→4)-Oligoglucans

Author(s): Jun-ichi Kadokawa*, Le Hooi Lee and Kazuya Yamamoto

Volume 25 , Issue 11 , 2021

Published on: 08 June, 2021

Page: [1345 - 1352] Pages: 8

DOI: 10.2174/1385272825666210607005208


Herein, the synthesis of 6-deoxygenated α(1→4)-oligoglucans via thermostable α- glucan phosphorylase (from Aquifex aeolicus VF5)-catalyzed enzymatic chain-elongation is reported from a maltotriose primer using a non-native substrate, 6-deoxy-α-D-glucose 1- phosphate. The enzymatic reaction of the two substrates mainly produced a tetrasaccharide with one 6-deoxy-α-D-glucose unit at the non-reducing end, together with a minor pentasaccharide with two 6-deoxy-α-D-glucose units. The enzymatic chain-elongation from the primer in the presence of 6-deoxy-α-D-glucose 1-phosphate and a native substrate, α-D-glucose 1- phosphate, afforded 6-deoxygenated α(1→4)-oligoglucans with varying degrees of polymerization. This enzymatic chain-elongation catalyzed by thermostable α-glucan phosphorylase is an efficient method to produce non-natural oligosaccharides, that is, 6-deoxygenated α(1→4)- oligoglucans.

Keywords: 6-Deoxygenated α(1→4)-oligoglucan, enzymatic chain-elongation, α-glucan phosphorylase, glycosylation, non-native substrate, maltooligosaccharide primer, non-natural oligosaccharide.

Graphical Abstract

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