Preparative-scale high-performance liquid chromatographic separation and purification of 3′-azido-3′-deoxythymidine-5′-phosphate

✍ Scribed by Joseph G. Turcotte; Philip E. Pivarnik; Shyam S. Shirali; Haribansh K. Singh; Raj K. Sehgal; Diane Macbride; Nan-In jang; Phyllis R. Brown

• Publisher: Elsevier Science
• Year: 1990
• Tongue: English
• Weight: 434 KB
• Volume: 499
• Category: Article
• ISSN: 1873-3778
• DOI: 10.1016/s0021-9673(00)96963-2

✦ Synopsis

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 ('H, i3C, 3 'P) 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.