Literature DB >> 2544857

The stereoselective enzymatic synthesis of 9-beta-D-2'-deoxyribofuranosyl 1-deazapurine.

D Betbeder1, D W Hutchinson, A O Richards.   

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.

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Year:  1989        PMID: 2544857      PMCID: PMC317930          DOI: 10.1093/nar/17.11.4217

Source DB:  PubMed          Journal:  Nucleic Acids Res        ISSN: 0305-1048            Impact factor:   16.971


  9 in total

1.  Purification, kinetics, and repression control of bacterial trans-N-deoxyribosylase.

Authors:  W S BECK; M LEVIN
Journal:  J Biol Chem       Date:  1963-02       Impact factor: 5.157

2.  Trans-N-deoxyribosylase from Lactobacillus helveticus. Crystallization and properties.

Authors:  W Uerkvitz
Journal:  Eur J Biochem       Date:  1971-11-11

3.  Relative potencies of anti-herpes compounds.

Authors:  P Collins; D J Bauer
Journal:  Ann N Y Acad Sci       Date:  1977-03-04       Impact factor: 5.691

4.  Analogs of 2'-deoxyadenosine: facile enzymatic preparation and growth inhibitory effects on human cell lines.

Authors:  M C Huang; K Hatfield; A W Roetker; J A Montgomery; R L Blakley
Journal:  Biochem Pharmacol       Date:  1981-10-01       Impact factor: 5.858

5.  Nucleoside deoxyribosyltransferase from Lactobacillus helveticus.

Authors:  R Cardinaud
Journal:  Methods Enzymol       Date:  1978       Impact factor: 1.600

6.  Synthesis of 2',3'-dideoxynucleosides by enzymatic trans-glycosylation.

Authors:  D A Carson; D B Wasson
Journal:  Biochem Biophys Res Commun       Date:  1988-09-15       Impact factor: 3.575

7.  Trans-N-deoxyribosylase: substrate specificity studies. Purine bases as acceptors.

Authors:  J Holguin; R Cardinaud
Journal:  Eur J Biochem       Date:  1975-06

8.  Deaza analogues of adenosine as inhibitors of blood platelet aggregation.

Authors:  I Antonini; G Cristalli; P Franchetti; M Grifantini; S Martelli; F Petrelli
Journal:  J Pharm Sci       Date:  1984-03       Impact factor: 3.534

9.  Metabolism and anti-human immunodeficiency virus-1 activity of 2-halo-2',3'-dideoxyadenosine derivatives.

Authors:  T Haertle; C J Carrera; D B Wasson; L C Sowers; D D Richman; D A Carson
Journal:  J Biol Chem       Date:  1988-04-25       Impact factor: 5.157

  9 in total

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