The stereoselective enzymatic synthesis of 9-beta-D-2'-deoxyribofuranosyl 1-deazapurine.
The transfer of 2-deoxyribose from thymidine to 1-deazapurine which is catalysed by N-deoxyribosyl transferases from Lactobacillus leichmanii occurs in high yield. This is a very stereoselective process and only one product, 9-beta-D-2'-deoxyribofuranosyl 1-deazapurine, is formed. Nmr spectroscopy, and in particular, nuclear Overhauser enhancement experiments, confirm that the 2-deoxyribose moiety is bound to N-9 rather than N-7 and that the glycosidic link has the beta-configuration.
Betbeder
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Department of Chemistry, University of Warwick, Coventry, UK.
Hutchinson
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Richards
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D000818:Animals; D002522:Chlorocebus aethiops; D003853:Deoxyribonucleosides / Q000138:chemical synthesis* / Q000494:pharmacology; D007778:Lactobacillus / Q000201:enzymology; D009682:Magnetic Resonance Spectroscopy; D010430:Pentosyltransferases; D018139:Simplexvirus / Q000187:drug effects; D013237:Stereoisomerism; D014709:Vero Cells; D014779:Virus Replication / Q000187:drug effects
D003853:Deoxyribonucleosides; C060162:2'-deoxyribofuranosyl-1-deazapurine; D010430:Pentosyltransferases; C021888:nucleoside deoxyribosyltransferase