Membrane-enclosed multienzyme (MEME) synthesis of 2, 7-anhydro-sialic acid derivatives. (8th November 2017)

• Record Type: Journal Article
• Authors: 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.; Juge, Nathalie
• Is Part Of: Carbohydrate research. Volume 451(2017)
• Page Start: 110
• Page End: 117
• Publication Date: 2017-11-08
• Subjects: Sialic acid enzymatic synthesis -- Ruminococcus gnavus -- Intramolecular trans-sialidase -- 2, 7-anhydro-Neu5Ac -- 2, 7-anhydro-Neu5Gc; Carbohydrates -- Periodicals; Chemistry, Organic -- Periodicals; Biochemistry -- Periodicals; Carbohydrates -- Periodicals; Chimie organique -- Périodiques; Glucides -- Périodiques; Biochemistry; Carbohydrates; Chemistry, Organic; Periodicals; Electronic journals; 507.78
• DOI: 10.1016/j.carres.2017.08.008
• Languages: English
• ISSNs: 0008-6215

Abstract

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. Graphical abstract: Membrane-enclosed multienzyme (MEME) approach for the production of 2, 7-anhydro-sialic acid derivatives. Highlights: A novel membrane enclosed multiple enzyme approach was developed for the production of 2, 7-anhydro-sialic acid derivatives. 2, 7-anhydro-Neu5Ac was produced in high-yield and high-purity. Neu5Gc-rich glycoprotein was produced using a one-pot two-step enzymatic synthesis. The method allowed the synthesis of a novel compound, 2, 7-anhydro-Neu5Gc.