Membrane-enclosed multienzyme (MEME) synthesis of 2,7-anhydro-sialic acid derivatives

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Monestier, Marie, Latousakis, Dimitrios, Bell, Andrew, Tribolo, Sandra, Tailford, Louise E., Colquhoun, Ian J., Le Gall, Gwenaelle, Yu, Hai, Chen, Xi, Rejzek, Martin, Dedola, Simone, Field, Robert A. and Juge, Nathalie (2017) Membrane-enclosed multienzyme (MEME) synthesis of 2,7-anhydro-sialic acid derivatives. Carbohydrate Research, 451. pp. 110-117. ISSN 0008-6215

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Abstract

Naturally occurring 2,7-anhydro-alpha-N-acetylneuraminic acid (2,7-anhydro-Neu5Ac) is a transglycosylation product of bacterial intramolecular trans-sialidases (IT-sialidases). A facile one-pot two-enzyme approach has been established for the synthesis of 2,7-anhydro-sialic acid derivatives including those containing different sialic acid forms such as Neu5Ac and N-glycolylneuraminic acid (Neu5Gc). The approach is based on the use of Ruminoccocus gnavus IT-sialidase for the release of 2,7-anhydro-sialic acid from glycoproteins, and the conversion of free sialic acid by a sialic acid aldolase. This synthetic method, which is based on a membrane-enclosed enzymatic synthesis, can be performed on a preparative scale. Using fetuin as a substrate, high-yield and cost-effective production of 2,7-anhydro-Neu5Ac was obtained to high-purity. This method was also applied to the synthesis of 2,7-anhydro-Neu5Gc. The membrane-enclosed multienzyme (MEME) strategy reported here provides an efficient approach to produce a variety of sialic acid derivatives.

Item Type: Article
Additional Information: Copyright © 2017 The Authors. Published by Elsevier Ltd.. All rights reserved.
Uncontrolled Keywords: sialic acid enzymatic synthesis,ruminococcus gnavus,intramolecular trans-sialidase,2,7-anhydro-neu5ac,2,7-anhydro-neu5gc
Faculty \ School: Faculty of Science > School of Chemistry, Pharmacy and Pharmacology
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Depositing User: Pure Connector
Date Deposited: 24 Aug 2017 05:06
Last Modified: 06 Feb 2025 07:23
URI: https://ueaeprints.uea.ac.uk/id/eprint/64652
DOI: 10.1016/j.carres.2017.08.008

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