Details
| Original language | English |
|---|---|
| Pages (from-to) | 314-318 |
| Number of pages | 5 |
| Journal | Advanced Synthesis and Catalysis |
| Volume | 349 |
| Issue number | 3 |
| Publication status | Published - Feb 2007 |
Abstract
The enzymatic epimerization of uridine 5′-diphospho-α-D-glucose (UDP-Glc, 1) and uridine 5′-diphospho-N-acetyl-α-D-glucosamine (UDPGlcNAc, 2) and the subsequent oxidation of uridine 5′-diphospho- α-D-galactose (UDP-Gal, 3) and uridine 5′-diphospho-N-acetyl- α-D-galactosamine (UDP-GalNAc, 4) were combined with chemical biotinylation with biotin-ε-amidocaproylhydrazide in a one-pot synthesis. Analysis by CE and NMR revealed a mixture (1.0:1.4) of the biotinylated nucleotide sugars uridine 5′-diphospho-6-biotin-ε- amidocaproylhydrazino-α-D-galactose (UDP-6-biotinyl-Gal, 7) and uridine 5′-diphospho-6-biotin-ε-amidocaproylhydrazino-α-D-glucose (UDP-6-biotinyl-Glc, 9), respectively, in a reaction started with 1. One product, uridine 5′-diphospho-6-biotin-ε-amidocaproylhydrazino-N- acetyl-α-D-galactosamine (UDP-6-biotinyl-GalNAc, 8) was formed when the reaction was initiated with 2. It could be demonstrated for the first time that a UDP-Glc(NAc) 4′-epimerase (Gne from Campylobacter jejuni) and galactose oxidase from Dactylium dendroides can be used simultaneously in enzymatic catalysis. This is of particular interest since the coaction of an enzyme demanding reductive conditions and an oxygen-dependent oxidase is unexpected.
Keywords
- Carbohydrates, Enzyme catalysis, Glycoconjugates, Glycosyltransferases, Oxidation
ASJC Scopus subject areas
- Chemical Engineering(all)
- Catalysis
- Chemistry(all)
- Organic Chemistry
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In: Advanced Synthesis and Catalysis, Vol. 349, No. 3, 02.2007, p. 314-318.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Combination of UDP-Glc(NAc) 4′-epimerase and galactose oxidase in a one-pot synthesis of biotinylated nucleotide sugars
AU - Namdjou, Darius J.
AU - Sauerzapfe, Birgit
AU - Schmiedel, Judith
AU - Dräger, Gerald
AU - Bernatchez, Stéphane
AU - Wakarchuk, Warren W.
AU - Elling, Lothar
N1 - Copyright: Copyright 2007 Elsevier B.V., All rights reserved.
PY - 2007/2
Y1 - 2007/2
N2 - The enzymatic epimerization of uridine 5′-diphospho-α-D-glucose (UDP-Glc, 1) and uridine 5′-diphospho-N-acetyl-α-D-glucosamine (UDPGlcNAc, 2) and the subsequent oxidation of uridine 5′-diphospho- α-D-galactose (UDP-Gal, 3) and uridine 5′-diphospho-N-acetyl- α-D-galactosamine (UDP-GalNAc, 4) were combined with chemical biotinylation with biotin-ε-amidocaproylhydrazide in a one-pot synthesis. Analysis by CE and NMR revealed a mixture (1.0:1.4) of the biotinylated nucleotide sugars uridine 5′-diphospho-6-biotin-ε- amidocaproylhydrazino-α-D-galactose (UDP-6-biotinyl-Gal, 7) and uridine 5′-diphospho-6-biotin-ε-amidocaproylhydrazino-α-D-glucose (UDP-6-biotinyl-Glc, 9), respectively, in a reaction started with 1. One product, uridine 5′-diphospho-6-biotin-ε-amidocaproylhydrazino-N- acetyl-α-D-galactosamine (UDP-6-biotinyl-GalNAc, 8) was formed when the reaction was initiated with 2. It could be demonstrated for the first time that a UDP-Glc(NAc) 4′-epimerase (Gne from Campylobacter jejuni) and galactose oxidase from Dactylium dendroides can be used simultaneously in enzymatic catalysis. This is of particular interest since the coaction of an enzyme demanding reductive conditions and an oxygen-dependent oxidase is unexpected.
AB - The enzymatic epimerization of uridine 5′-diphospho-α-D-glucose (UDP-Glc, 1) and uridine 5′-diphospho-N-acetyl-α-D-glucosamine (UDPGlcNAc, 2) and the subsequent oxidation of uridine 5′-diphospho- α-D-galactose (UDP-Gal, 3) and uridine 5′-diphospho-N-acetyl- α-D-galactosamine (UDP-GalNAc, 4) were combined with chemical biotinylation with biotin-ε-amidocaproylhydrazide in a one-pot synthesis. Analysis by CE and NMR revealed a mixture (1.0:1.4) of the biotinylated nucleotide sugars uridine 5′-diphospho-6-biotin-ε- amidocaproylhydrazino-α-D-galactose (UDP-6-biotinyl-Gal, 7) and uridine 5′-diphospho-6-biotin-ε-amidocaproylhydrazino-α-D-glucose (UDP-6-biotinyl-Glc, 9), respectively, in a reaction started with 1. One product, uridine 5′-diphospho-6-biotin-ε-amidocaproylhydrazino-N- acetyl-α-D-galactosamine (UDP-6-biotinyl-GalNAc, 8) was formed when the reaction was initiated with 2. It could be demonstrated for the first time that a UDP-Glc(NAc) 4′-epimerase (Gne from Campylobacter jejuni) and galactose oxidase from Dactylium dendroides can be used simultaneously in enzymatic catalysis. This is of particular interest since the coaction of an enzyme demanding reductive conditions and an oxygen-dependent oxidase is unexpected.
KW - Carbohydrates
KW - Enzyme catalysis
KW - Glycoconjugates
KW - Glycosyltransferases
KW - Oxidation
UR - http://www.scopus.com/inward/record.url?scp=34547232023&partnerID=8YFLogxK
U2 - 10.1002/adsc.200606169
DO - 10.1002/adsc.200606169
M3 - Article
AN - SCOPUS:34547232023
VL - 349
SP - 314
EP - 318
JO - Advanced Synthesis and Catalysis
JF - Advanced Synthesis and Catalysis
SN - 1615-4150
IS - 3
ER -