title: Purification of PMPA amidate prodrugs by SMB chromatography and x-ray crystallography of the diastereomerically pure GS-7340.
abstract: The diastereomers of GS-7171, aryl phosphoramidate derivatives of the anti-HIV nucleotide analog 9-[2-R-(phosphonomethoxy)propyl]adenine (tenofovir, PMPA), were isolated by batch elution chromatography and continuous simulated moving bed chromatography. The absolute configuration of the more pharmacologically active diastereomer, GS-7340, was determined to be (R,S,S) by single crystal x-ray crystallography.
authors.affiliation: Gilead Sciences Inc., Foster City, California, USA.
authors.forename: H
authors.initials: H
authors.lastname: Chapman
authors.forename: M
authors.initials: M
authors.lastname: Kernan
authors.forename: J
authors.initials: J
authors.lastname: Rohloff
authors.forename: M
authors.initials: M
authors.lastname: Sparacino
authors.forename: T
authors.initials: T
authors.lastname: Terhorst
mesh_terms: D000225:Adenine / Q000031:analogs & derivatives* / Q000737:chemistry* / Q000302:isolation & purification*; D000409:Alanine; D019380:Anti-HIV Agents / Q000737:chemistry / Q000302:isolation & purification*; D002845:Chromatography / Q000379:methods; D018360:Crystallography, X-Ray; D063065:Organophosphonates; D009943:Organophosphorus Compounds / Q000737:chemistry* / Q000302:isolation & purification; D011355:Prodrugs / Q000737:chemistry / Q000302:isolation & purification*; D013237:Stereoisomerism; D000068698:Tenofovir / Q000031:analogs & derivatives
chemical_list: D019380:Anti-HIV Agents; D063065:Organophosphonates; D009943:Organophosphorus Compounds; D011355:Prodrugs; D000068698:Tenofovir; C442442:tenofovir alafenamide; D000225:Adenine; D000409:Alanine