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Nucleic Acids Research, 1989, Vol. 17, No. 11 4217-4222
© 1989

CHEMISTRY

The stereoselective enzymatic synthesis of 9-ß-d-2'-deoxyribofuranosyl 1-deazapurine

D. Betbeder, D.W. Hutchinson and A.O'L. Richards

Department of Chemistry, University of Warwick Coventry CV4 7AL, UK

Received March 22, 1989. Revised April 28, 1989. Accepted April 28, 1989.

The transfer of 2-deoxyribose from thymidine to 1-deazapurine which is catalysed by N-deoxyribosyl transferases from Lactobadllus leichmanii occurs in high yield. This is a very stereoselective process and only one product, 9-ß-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 ß-configuration.


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