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• W1975161429 abstract "Abstract Nucleotides 2-(4-azidophenacyl)thio-1,N6-etheno-2′-deoxyadenosine 5′-triphosphate 1 and its tetrafluoro analog 2 inhibit HIV-1 reverse transcriptase (RT) competitively relative to template. These template-competitive RT inhibitors (TCRTIs) were analyzed for conformational properties by molecular modeling and NMR analysis. Both inhibitors prefer sugar conformations of C2′-endo/C3′-exo with a high-anti glycosidic bond rotation and +sc/ap phosphate conformation (γ). The major effect of the etheno group is to favor an extended, fully staggered anti conformation in the N1-C2-S-CH2 ψ 1 side chain rotation, and NMR analysis detects a long range sugar H4′ to side chain phenyl meta-H NOE, a result consistent with this compact structure as an important contributor to the solution structure. The binding model generated places the phenyl side chain in a lipophilic pocket in the template grip region of the RT polymerase domain with the Mg-triphosphate complexed to active site carboxylates. The structures of the TCRTIs are compared with that of the template-competitive DNA polymerase inhibitor 2-(4-azidophenacyl)thio-2′-deoxyadenosine 5′-triphosphate 3, and a theoretical model for selectivity is proposed." @default.
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• W1975161429 date "2003-06-01" @default.
• W1975161429 modified "2023-10-18" @default.
• W1975161429 title "Conformational Properties of Nucleotide-Based Template-Competitive HIV-1 Reverse Transcriptase Inhibitors: Analysis of Enzyme Binding Modes" @default.
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• W1975161429 doi "https://doi.org/10.1081/ncn-120021428" @default.
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