Issue 11, 2019

Gram scale production of 1-azido-β-d-glucose via enzyme catalysis for the synthesis of 1,2,3-triazole-glucosides

Abstract

The production of analytical amounts of azido sugars is used as a means of verifying catalytic acid/base mutations of retaining glycosidase, but application of this process to preparative synthesis has not been reported. The catalytic acid/base mutant of Thermoanaerobacterium xylanolyticus GH116 β-glucosidase, TxGH116D593A, catalyzed the gram scale production of 1-azido-β-D-glucose (1) from p-nitropheyl-β-D-glucopyranoside (pNPGlc) and azide via a transglucosylation reaction. Overnight reaction of the enzyme with pNPGlc and NaN3 in aqueous MES buffer (pH 5.5) at 55 °C produced 1 (3.27 g), which was isolated as a white foamy solid in 96% yield. This 1 was successfully utilized for the synthesis of fifteen 1,2,3-triazole-β-D-glucosyl derivatives (2–16) containing a variety of functional groups, via click chemistry.

Graphical abstract: Gram scale production of 1-azido-β-d-glucose via enzyme catalysis for the synthesis of 1,2,3-triazole-glucosides

Supplementary files

Article information

Article type
Paper
Submitted
28 Jan 2019
Accepted
14 Feb 2019
First published
20 Feb 2019
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2019,9, 6211-6220

Gram scale production of 1-azido-β-D-glucose via enzyme catalysis for the synthesis of 1,2,3-triazole-glucosides

J. N. Gorantla, S. Pengthaisong, S. Choknud, T. Kaewpuang, T. Manyum, V. Promarak and J. R. Ketudat Cairns, RSC Adv., 2019, 9, 6211 DOI: 10.1039/C9RA00736A

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