A phosphoramidite-based synthesis of phosphoramidate amino acid diesters of antiviral nucleosides

Timothy W. Abraham, Carston R. Wagner

Research output: Contribution to journalArticlepeer-review

44 Scopus citations

Abstract

A general synthetic procedure is presented for the preparation of 5’-amino acid phosphoramidates of zidovudine (AZT), 3’-deoxy-2’,3’-didehydro-thymidine (D4T), and 3'-fluoro-3’-deoxythymidine (FLT) from their corresponding phosphoramidites. These water soluble amino acid phosphoramidates are more non-polar than the parent nucleoside and exhibit high stability in aqueous media.

Original languageEnglish (US)
Pages (from-to)1891-1903
Number of pages13
JournalNucleosides and Nucleotides
Volume13
Issue number9
DOIs
StatePublished - Sep 1 1994

Bibliographical note

Funding Information:
We wish to thank Dr. George Ellestad and American Cyanamid for their kind gift of FLT, Mr. Edward McIntee for carrying out the stability studies on the phosphoramidates, and Ms. Laura Wiebers for her thorough reading of this manuscript. We also wish to thank the American Cancer Society (IN-13-33-20) and NIH (CA61909) for partial support of this study.

Copyright:
Copyright 2015 Elsevier B.V., All rights reserved.

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