Synthesis of P1-(11-phenoxyundecyl)-P2-(2-acetamido-2-deoxy-3-O-α-D-rhamnopyranosyl-α-D-glucopyranosyl) diphosphate and P1-(11-phenoxyundecyl)-P2-(2-acetamido-2-deoxy-3-O-β-D-galactopyranosyl-α-D-galactopyranosyl) diphosphate for the investigation of biosynthesis of O-antigenic polysaccharides in Pseudomonas aeruginosa and Escherichia coli O104. (1st December 2017)

• Record Type: Journal Article
• Authors: Torgov, Vladimir; Danilov, Leonid; Utkina, Natalia; Veselovsky, Vladimir; Brockhausen, Inka
• Is Part Of: Carbohydrate research. Volume 453/454(2017)
• Page Start: 19
• Page End: 25
• Publication Date: 2017-12-01
• Subjects: P1- (11-phenoxyundecyl) -P2-(2-acetamido-2-deoxy-3-O-α-D-rhamnopyranosyl-α-D-glucopyranosyl) diphosphate -- P1-(11-phenoxyundecyl) -P2-(2-acetamido-2-deoxy-3-O-β-D-galactopyranosyl-α-D-galactopyranosyl) diphosphate -- Chemical synthesis -- Enterobacterial glycosyltransferases -- Pseudomonas aeruginosa -- Escherichia coli O104; 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.2017.10.016
• Languages: English
• ISSNs: 0008-6215

Abstract

Abstract: Two new phenoxyundecyl diphosphate sugars were synthesized for the first time: P 1 -(11-phenoxyundecyl)-P 2 - (2-acetamido-2-deoxy-3- O -α-D -rhamnopyranosyl-α-D -glucopyranosyl) diphosphate and P 1 -(11-phenoxyundecyl)-P 2 -(2-acetamido-2-deoxy-3- O -β-D -galactopyranosyl-α-D -galactopyranosyl) diphosphate to study the third step of biosynthesis of the repeating units of O-antigenic polysaccharides in Pseudomonas aeruginosa and E.coli O104 respectively. Graphical abstract: Highlights: Two phenoxyundecyl diphosphate disaccharides were synthesized. The structures were confirmed by NMR and HRESIMS data. Diphosphates 1 and 2 are substrates for P.aeruginosa and E.coli glycosyltransferases.