title: The triphosphate of beta-D-4'-C-ethynyl-2',3'-dideoxycytidine is the preferred enantiomer substrate for HIV reverse transcriptase.
abstract: The enantioselective synthesis of the beta-d (1) enantiomer of 4'-C-ethynyl-2',3'-dideoxycytidine confirms an earlier stereochemical assignment that was strictly based on the ability of HIV reverse transcriptase and its M184V mutant to discriminate between the d- and l-configuration of nucleoside 5'-triphosphates.
authors.affiliation: Laboratory of Medicinal Chemistry, Center for Cancer Research, NCI-Frederick, NIH, Frederick, MD 21702, USA.
authors.forename: Maqbool A
authors.initials: MA
authors.lastname: Siddiqui
authors.forename: Victor E
authors.initials: VE
authors.lastname: Marquez
mesh_terms: D054303:HIV Reverse Transcriptase / Q000737:chemistry*; D015394:Molecular Structure; D009705:Nucleosides / Q000737:chemistry; D011122:Polyphosphates / Q000737:chemistry*; D018894:Reverse Transcriptase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013379:Substrate Specificity; D016047:Zalcitabine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D009705:Nucleosides; D011122:Polyphosphates; D018894:Reverse Transcriptase Inhibitors; C517092:beta-D-4'-C-ethynyl-2',3'-dideoxycytidine; D016047:Zalcitabine; D054303:HIV Reverse Transcriptase; C005692:triphosphoric acid