Preparation of Imino and Amino N-15 Enriched 2-Aminopurine Deoxynucleoside

Lawrence C. Sowers Departments of Biological Sciences, Molecular Biology Section, University of Southern California, University Park, Los Angeles, CA, 90089-1481; Division of Pediatrics, City of Hope National Medical Center, 1500 E. Duarte Road, Duarte, CA, 91010

Dhananjaya N. Mhaskar Departments of Biological Sciences, Molecular Biology Section, University of Southern California, University Park, Los Angeles, CA, 90089-1481

Tasneem A. Khwaja Departments of Pathology and Comprehensive Cancer Center, University of Southern California, 1303′Mission Road, Los Angeles, CA, 90033

Myron F. Goodman Departments of Biological Sciences, Molecular Biology Section, University of Southern California, University Park, Los Angeles, CA, 90089-1481

Abstract

We report the synthesis of N-15 enriched 2-aminopurine-2′-deoxynucleoside (APdR). Both ring and 2-amino nitrogens were labelled via a Dimroth rearrangement of the free base. The corresponding deoxynucleoside was prepared enzymatically. Results of both proton and N-15 NMR studies show that the predominant tautomeric form of APdR is amino and the N1 position is shown to be the site of protonation.

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Preparation of Imino and Amino N-15 Enriched 2-Aminopurine Deoxynucleoside

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Preparation of Imino and Amino N-15 Enriched 2-Aminopurine Deoxynucleoside

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