Immobilization of UDP‐Galactose on an Amphiphilic Resin

• Published in: European journal of organic chemistry Vol. 2018; no. 7; pp. 908 - 914
• Main Authors: Bevan, Jessica G. M., Lourenço, Eva C., Chaves‐Ferreira, Miguel, Rodrigues, João A., Rita Ventura, M.
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 21.02.2018; Wiley Subscription Services, Inc
• Subjects: Amphiphilic resin; Carbohydrates; Chemistry; Chemistry, Organic; Conjugation; Fluorination; Galactose; Glycosylation; Immobilization; Physical Sciences; Polyethylene glycol; Science & Technology; Sugar; UDP‐Galactose; Carbohydrates; ANALOGS; DIPHOSPHATE; N-GLYCANS; Immobilization; EFFICIENT SYNTHESIS; Glycosylation; CELL-ADHESION; SUGARS; INHIBITION; MANNOSE; ESTERS; Amphiphilic resin; UDP-Galactose; POTASSIUM
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.201701620

Nucleotide sugars are activated sugar precursors used by glycosyltransferases to form glycans. Here we report the first examples of resin‐bound nucleotide sugars: fluorinated UDP‐galactose and UDP‐galactose. They were conjugated to a polyethylene glycol resin through the C6 position with an SMCC linker in good to excellent yields. This synthesis represents an efficient method to access resin‐bound nucleotide sugars in a modular approach that enables modifications of the sugar or nucleotide before conjugation. The system has been conceived as a new chemistry‐based screening system for enzymes that use UDP‐galactose. Here we report the first example of resin‐bound nucleotide sugars: fluorinated UDP‐Galactose and UDP‐Galactose. This synthesis represents an efficient method to access resin‐bound nucleotide sugars in a modular approach that enables modifications of the sugar or nucleotide before conjugation.