Novel benzyl rearrangements in electrospray ionization multistage tandem mass spectra of benzyl 2',3'- didehydro-2',3'-dideoxythymidin-5'-yl H-phosphonate.
Several alkyl 2',3'-didehydro-2',3'-dideoxythymidin-5'-yl H-phosphonates were synthesized and analyzed by electrospray ionization multistage tandem mass spectrometry (ESI-MS(n)). Two kinds of novel benzyl rearrangement reactions were observed in ESI - MS(2) of [M + H](+), [M + Na](+) and [M + K](+) of benzyl 2',3'-didehydro-2',3'-dideoxythymidin-5' yl H-phosphonate. Results from tandem mass spectrometry, high-resolution mass spectrometry and control experiments showed that the benzyl migration could undergo a four-membered cyclic rearrangement reaction, and benzyl was essential in the process.
Chen
Yi
Y
Key Laboratory of Chemical Biology, Chemistry Department, Zhengzhou University, 450052, China.
Sun
Xiaobin
X
Fu
Hua
H
Liu
Xiaohong
X
Zhao
Yufen
Y
D019380:Anti-HIV Agents / Q000737:chemistry*; D018894:Reverse Transcriptase Inhibitors / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization / Q000379:methods*; D018119:Stavudine / Q000031:analogs & derivatives* / Q000737:chemistry*
D019380:Anti-HIV Agents; D018894:Reverse Transcriptase Inhibitors; D018119:Stavudine