title: The stereoselective enzymatic synthesis of 9-beta-D-2'-deoxyribofuranosyl 1-deazapurine.
abstract: 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.
authors.affiliation: Department of Chemistry, University of Warwick, Coventry, UK.
authors.forename: D
authors.initials: D
authors.lastname: Betbeder
authors.forename: D W
authors.initials: DW
authors.lastname: Hutchinson
authors.forename: A O
authors.initials: AO
authors.lastname: Richards
mesh_terms: 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
chemical_list: D003853:Deoxyribonucleosides; C060162:2'-deoxyribofuranosyl-1-deazapurine; D010430:Pentosyltransferases; C021888:nucleoside deoxyribosyltransferase