Document Detail


Synthesis of 4- and 5-amino-1-(2-deoxy-D-erythro-pentofuranosyl)imidazole nucleosides by chemical and biotransformation methods.
MedLine Citation:
PMID:  1797375     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
(2-Deoxy-D-erythro-pentofuranosyl)imidazole nucleosides have been synthesised by glycosylation of the sodium salt of ethyl 5-aminoimidazole-4-carboxylate with 2-deoxy-3,5-di-O-p-toluoyl-alpha-D-erythro-pentofuranosyl chloride. Glycosylation of ethyl 5-aminoimidazole-4-carboxylate with 2-deoxy-beta-D-erythro-pentofuranose was also achieved enzymically using E. coli, immobilised by ionotropic gelation in an alginate gel, with 2'-deoxyuridine as glycosyl donor. 5-Amino-1-(2-deoxy-beta-D-erythro-pentofuranosyl)imidazole-4-carboxylic acid 5'-phosphate and 4-amino-1-(2-deoxy-beta-D-erythro-pentofuranosyl)imidazole-5-carboxylic acid 5'-phosphate were synthesised by phosphorylation of the respective nucleosides and examined as inhibitors of phosphoribosylaminoimidazole carboxylase (EC 4.1.1.21) and phosphoribosylaminoimidazolesuccinocarboxamide synthetase (EC 6.3.2.6), which are involved in the de novo biosynthesis of purine nucleotides.
Authors:
D F Ewing; A Holý; I Votruba; R W Humble; G Mackenzie; F Hewedi; G Shaw
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Carbohydrate research     Volume:  216     ISSN:  0008-6215     ISO Abbreviation:  Carbohydr. Res.     Publication Date:  1991 Sep 
Date Detail:
Created Date:  1992-04-14     Completed Date:  1992-04-14     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  0043535     Medline TA:  Carbohydr Res     Country:  NETHERLANDS    
Other Details:
Languages:  eng     Pagination:  109-18     Citation Subset:  IM    
Affiliation:
School of Chemistry, University of Hull, Great Britain.
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MeSH Terms
Descriptor/Qualifier:
Biotransformation
Carboxy-Lyases / metabolism
Escherichia coli / enzymology
Kinetics
Magnetic Resonance Spectroscopy
Molecular Structure
Nucleosides / biosynthesis,  chemical synthesis*,  chemistry
Peptide Synthases / metabolism
Chemical
Reg. No./Substance:
0/Nucleosides; EC 4.1.1.-/Carboxy-Lyases; EC 4.1.1.21/phosphoribosylaminoimidazole carboxylase; EC 6.3.2.-/Peptide Synthases; EC 6.3.2.6/phosphoribosylaminoimidazole-succinocarboxamide synthetase

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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