3'-azidothymidine-5'-(phenylmethoxyalanyl)phosphate

Azt-pmap, a nucleoside analogue, is an aryl phosphate derivative of AZT. Azt-pmap shows anti-HIV activity[1]. AZT is a nucleoside reverse transcriptase inhibitor (NRTI) for HIV infection[2]. Azt-pmap is a click chemistry reagent, it contains an Azide group and can undergo copper-catalyzed azide-alkyne cycloaddition reaction (CuAAc) with molecules containing Alkyne groups. It can also undergo strain-promoted alkyne-azide cycloaddition (SPAAC) reactions with molecules containing DBCO or BCN groups.

HIV-1

[1] McGuigan C, et al. Aryl phosphate derivatives of AZT retain activity against HIV1 in cell lines which are resistant to the action of AZT. Antiviral Res. 1992 Apr;17(4):311-21. DOI:10.1016/0166-3542(92)90026-2
[2] Gray LR, et al. The NRTIs lamivudine, stavudine and zidovudine have reduced HIV-1 inhibitory activity in astrocytes. PLoS One. 2013 Apr 16;8(4):e62196. DOI:10.1371/journal.pone.0062196