Yi Chen, Yingwu Yin, Xiaobin Sun
May 1, 2005
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Influential Citations
17
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Journal
Journal of mass spectrometry : JMS
Abstract
Several amino acid ester cyclohexyl phosphoramidates of AZT as anti-HIV prodrugs were synthesized and investigated by electrospray ionization tandem mass spectrometry (ESI-MS(n)). A novel methoxy group migration from the carbonyl group to the phosphoryl group was observed in ESI-MS2. This migration is believed to be a general pathway for ions with a methyl ester moiety at the gamma-position to a phosphoric acid moiety, which is assisted with metal ions such as Li(+), Na(+) and K(+). Coordination between metal ions with both the carbonyl oxygen and phosphoryl oxygen might be a key factor responsible for this migration.