Purification of PMPA amidate prodrugs by SMB chromatography and x-ray crystallography of the diastereomerically pure GS-7340.
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.
Chapman
H
H
Gilead Sciences Inc., Foster City, California, USA.
Kernan
M
M
Rohloff
J
J
Sparacino
M
M
Terhorst
T
T
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
D019380:Anti-HIV Agents; D063065:Organophosphonates; D009943:Organophosphorus Compounds; D011355:Prodrugs; D000068698:Tenofovir; C442442:tenofovir alafenamide; D000225:Adenine; D000409:Alanine