title: Preparative-scale high-performance liquid chromatographic separation and purification of 3'-azido-3'-deoxythymidine-5'-phosphate.
abstract: Crude 3'-azido-3'-deoxythymidine-5'-phosphate (AZT-P), obtained from direct phosphorylation of 3'-azido-3'-deoxythymidine (azidothymidine, AZT), was separated and purified by isocratic preparative high-performance liquid chromatography. The components in a 2.5-g load of crude AZT-P, obtained from work-up of the phosphorylation reaction, were separated in 50 min to give 1.8 g of 99.5% pure AZT-P. AZT-P was analyzed by high-performance liquid chromatography and by high-resolution nuclear magnetic resonance (1H, 13C, 31P) spectroscopy. The practical and rapid preparative chromatographic method is being applied to the purification of AZT-P and other antiretroviral dideoxynucleotides, used as intermediates in the synthesis of target-directed experimental drugs for the treatment of AIDS.
authors.affiliation: Department of Medicinal Chemistry, University of Rhode Island, Kingston 02881.
authors.forename: J G
authors.initials: JG
authors.lastname: Turcotte
authors.forename: P E
authors.initials: PE
authors.lastname: Pivarnik
authors.forename: S S
authors.initials: SS
authors.lastname: Shirali
authors.forename: H K
authors.initials: HK
authors.lastname: Singh
authors.forename: R K
authors.initials: RK
authors.lastname: Sehgal
authors.forename: D
authors.initials: D
authors.lastname: Macbride
authors.forename: N I
authors.initials: NI
authors.lastname: Jang
authors.forename: P R
authors.initials: PR
authors.lastname: Brown
mesh_terms: D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D054306:Dideoxynucleotides; D013942:Thymine Nucleotides; D015215:Zidovudine / Q000031:analogs & derivatives* / Q000302:isolation & purification / Q000378:metabolism
chemical_list: D054306:Dideoxynucleotides; D013942:Thymine Nucleotides; C057287:3'-azido-3'-deoxythymidine 5'phosphate; D015215:Zidovudine