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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