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

Marie Monestier, Dimitrios Latousakis, Andrew Bell, Sandra Tribolo, Louise E Tailford, Ian J Colquhoun, Gwenaelle Le Gall, Hai Yu, Xi Chen, Martin Rejzek, Simone Dedola, Robert A Field, Nathalie Juge

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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.
Original languageEnglish
Pages (from-to)110-117
Number of pages8
JournalCarbohydrate Research
Volume451
Early online date19 Aug 2017
DOIs
Publication statusPublished - 8 Nov 2017
Externally publishedYes

Keywords

  • Sialic acid enzymatic synthesis
  • Ruminococcus gnavus
  • Intramolecular trans-sialidase
  • 2,7-anhydro-Neu5Ac
  • 2,7-anhydro-Neu5Gc

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