Membrane-enclosed multienzyme (MEME) synthesis of 2,7-anhydro-sialic acid derivatives
| Autor: | Louise E. Tailford, Gwénaëlle Le Gall, Simone Dedola, Sandra Tribolo, Robert A. Field, Dimitrios Latousakis, Xi Chen, Marie Monestier, Martin Rejzek, Hai Yu, Andrew Bell, Nathalie Juge, Ian J. Colquhoun |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
0301 basic medicine
Stereochemistry Neuraminidase Sialic acid enzymatic synthesis 01 natural sciences Biochemistry Article Analytical Chemistry 03 medical and health sciences chemistry.chemical_compound Ruminococcus gnavus Manchester Institute of Biotechnology Ruminococcus Intramolecular trans-sialidase Glycoproteins chemistry.chemical_classification 010405 organic chemistry Chemistry Organic Chemistry 2 7-anhydro-Neu5Gc Substrate (chemistry) General Medicine Enzymatic synthesis ResearchInstitutes_Networks_Beacons/manchester_institute_of_biotechnology 2 7-anhydro-Neu5Ac Fetuin N-Acetylneuraminic Acid 0104 chemical sciences Sialic acid 030104 developmental biology Membrane Intramolecular force Glycoprotein |
| Zdroj: | Monestier, M, Latousakis, D, Bell, A, Tribolo, S, Tailford, L E, Colquhoun, I J, Gall, G L, Yu, H, Chen, X, Rejzek, M, Dedola, S, Field, R A & Juge, N 2017, ' Membrane-enclosed multienzyme (MEME) synthesis of 2,7-anhydro-sialic acid derivatives ', Carbohydrate Research . https://doi.org/10.1016/j.carres.2017.08.008 Carbohydrate Research |
| ISSN: | 0008-6215 |
| DOI: | 10.1016/j.carres.2017.08.008 |
| Popis: | 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.Image 1 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. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|
Full Text from ScienceDirect