Title: Phosphoramidate derivatives of d4T as inhibitors of HIV: the effect of amino acid variation
Authors: McGuigan, C ×
Tsang, H W
Cahard, D
Turner, K
Velazquez, S
Salgado, A
Bidois, L
Naesens, Lieve
De Clercq, Erik
Balzarini, Jan #
Issue Date: Aug-1997
Series Title: Antiviral research vol:35 issue:3 pages:195-204
Abstract: Phosphoramidate derivatives of the nucleoside analogue, 2',3'-dideoxy-2',3'-didehydro thymidine (d4T) have been prepared as potential membrane-soluble pro-drugs of the big-active free phosphate forms. In particular phenyl phosphates, linked via nitrogen to methyl-esterified amino acids, were studied. All compounds were fully characterised by a range of methods (high-field multinuclear NMR, mass spectrometry and high performance liquid chromatography (HPLC)) and were subjected to in vitro evaluation of their anti-HIV efficacy. The nature of the amino acid appeared to be extremely important for the eventual antiviral action. Of the amino acids studied, L-alanine was the most efficacious, whilst L-proline and glycine were particularly poor. However, an unnatural amino acid moiety, dimethylglycine, could substitute for alanine with little or no loss of activity.
ISSN: 0166-3542
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Laboratory of Virology and Chemotherapy (Rega Institute)
× corresponding author
# (joint) last author

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