Immobilization of UDP‐Galactose on an Amphiphilic Resin

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 lin...

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Veröffentlicht in:European journal of organic chemistry Jg. 2018; H. 7; S. 908 - 914
Hauptverfasser: Bevan, Jessica G. M., Lourenço, Eva C., Chaves‐Ferreira, Miguel, Rodrigues, João A., Rita Ventura, M.
Format: Journal Article
Sprache:Englisch
Veröffentlicht: WEINHEIM Wiley 21.02.2018
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Schlagworte:
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
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Zusammenfassung: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.
Bibliographie:FCT
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SourceType-Scholarly Journals-1
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content type line 14
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201701620