Synthesis of unnatural sugar nucleotides and their evaluation as donor substrates in glycosyltransferase-catalyzed reactions
| ISSN: | 0008-6215 |
|---|---|
| DOI: | 10.1016/j.carres.2004.09.002 |
| Přístupová URL adresa: | https://explore.openaire.eu/search/publication?articleId=doi_dedup___::c37c6d82e801a2e0d748efcca10ff5ee https://doi.org/10.1016/j.carres.2004.09.002 |
| Rights: | CLOSED |
| Přírůstkové číslo: | edsair.doi.dedup.....c37c6d82e801a2e0d748efcca10ff5ee |
| Autor: | Claudine Augé, Tatiana Ivannikova, Amira Khaled |
| Rok vydání: | 2004 |
| Předmět: |
Stereochemistry
N-Acetylglucosaminyltransferases Biochemistry Catalysis Fucose Substrate Specificity Analytical Chemistry Structure-Activity Relationship chemistry.chemical_compound Bacterial Proteins Glycosyltransferase Transferase Nucleotide chemistry.chemical_classification biology Nucleoside Diphosphate Sugars Chemistry Organic Chemistry Glycosyltransferases Substrate (chemistry) Adenosine Diphosphate Sugars General Medicine Fucosyltransferases Uridine Diphosphate Sugars carbohydrates (lipids) Kinetics Yield (chemistry) biology.protein Cyanuric acid Derivative (chemistry) |
| Zdroj: | Carbohydrate Research. 339:2641-2649 |
| ISSN: | 0008-6215 |
| DOI: | 10.1016/j.carres.2004.09.002 |
| Popis: | New unnatural sugar nucleotides, UDP-Fuc and CDP-Fuc were synthesized from fucose-beta-1-phosphate and nucleotide monophosphates activated as morpholidates. Furthermore, a nucleotide analogue was prepared by phosphorylation of 1-(beta-D-ribofuranosyl)cyanuric acid, itself obtained as a protected derivative by condensation of the persilylated derivative of cyanuric acid with 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose in 74% yield. This phosphate activated according to the same procedure was condensed with fucose-beta-1-phosphate, affording a new sugar nucleotide conjugate (NDP-Fuc) which was evaluated together with UDP-Fuc, CDP-Fuc and ADP-Fuc, as fucose donors in alpha-(1-->4/3)-fucosyltransferase (FucT-III) catalyzed reaction. Fucose transfer could be observed with each of the donors and kinetic parameters were determined using a fluorescent acceptor substrate. Efficiency of the four analogues towards FucT-III was in the following order: UDP-Fuc=ADP-Fuc>NDP-Fuc>CDP-Fuc. According to the same strategy ADP-GlcNAc was prepared from AMP-morpholidate and N-acetylglucosamine-alpha-1-phosphate; tested as a glucosaminyl donor towards Neisseria meningitidis N-acetylglucosaminyl transferase (LgtA), ADP-GlcNAc was recognized with 0.1% efficiency as compared with UDP-GlcNAc, the natural donor substrate. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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