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  • Title: Synthesis of 2',3'-dideoxynucleosides by enzymatic trans-glycosylation.
    Author: Carson DA, Wasson DB.
    Journal: Biochem Biophys Res Commun; 1988 Sep 15; 155(2):829-34. PubMed ID: 3262341.
    Abstract:
    Recently, several pyrimidine and purine 2',3'-dideoxynucleosides have been shown to inhibit the replication of the human immunodeficiency virus-1 (HIV), the causative agent of the acquired immune deficiency syndrome (AIDS). These compounds are usually prepared by reduction of the corresponding 2'-deoxynucleosides. The present experiments demonstrate that 2',3'-dideoxynucleosides can also be made by enzymatic trans-glycosylation, using the trans-N-deoxyribosylase from Lactobacillus helveticus. The broad specificity of this enzyme makes it possible to synthesize for metabolic studies radiochemically pure 2',3'-dideoxynucleosides, using diverse purine and pyrimidine base acceptors.
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