Synthesis of prodrug candidates: conjugates of amino acid with nucleoside boranophosphate.
[structure: see text] Preparation of antiviral and anticancer prodrug candidates, P-tyrosinyl(P-O)-5'-P-nucleosidyl boranophosphates, is described. One-pot synthesis via a phosphoramidite method resulted in the title compounds with good yields. The P-boranophosphate diastereomers were separated by RP-HPLC, and their structures were confirmed by 1H and 31P NMR spectroscopy and MS analysis.
Li
Ping
P
Department of Chemistry, Box 90346, Duke University, Durham, North Carolina 27708-0346, USA.
Shaw
Barbara Ramsay
BR
D000596:Amino Acids / Q000737:chemistry*; D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D000998:Antiviral Agents / Q000138:chemical synthesis*; D002851:Chromatography, High Pressure Liquid; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D009705:Nucleosides / Q000737:chemistry; D010710:Phosphates / Q000737:chemistry*; D011355:Prodrugs / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000596:Amino Acids; D000970:Antineoplastic Agents; D000998:Antiviral Agents; D009705:Nucleosides; D010710:Phosphates; D011355:Prodrugs