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

Timothy W. Abraham; Carston R. Wagner

doi:10.1080/15257779408010671

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

Timothy W. Abraham, Carston R. Wagner

Medicinal Chemistry

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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 language	English (US)
Pages (from-to)	1891-1903
Number of pages	13
Journal	Nucleosides and Nucleotides
Volume	13
Issue number	9
DOIs	https://doi.org/10.1080/15257779408010671
State	Published - 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.

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abstract = "A general synthetic procedure is presented for the preparation of 5{\textquoteright}-amino acid phosphoramidates of zidovudine (AZT), 3{\textquoteright}-deoxy-2{\textquoteright},3{\textquoteright}-didehydro-thymidine (D4T), and 3'-fluoro-3{\textquoteright}-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.",

author = "Abraham, {Timothy W.} and Wagner, {Carston R.}",

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.",

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doi = "10.1080/15257779408010671",

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PY - 1994/9/1

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N2 - 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.

AB - 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.

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

Abstract

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