Literature DB >> 20044271

A novel rearrangement of fluorescent human thymidylate synthase inhibitor analogues in ESI tandem mass spectrometry.

Yi Chen1, Céline Le Droumaguet, Kai Li, William E Cotham, Norman Lee, Mike Walla, Qian Wang.   

Abstract

Cu(I) catalyzed alkyne-azide cycloaddition reaction was employed to synthesize a series of anthracene-based human thymidylate synthase (hTS) inhibitor analogues. The triazolo-anthracene derivatives were characterized by ESI-MS/MS and a novel rearrangement reaction in ESI-MS/MS was observed. The mechanism is proposed whereby the protonated triazolo-anthracene derivative forms a carbocation, and then the carbocation electrophilically attacks an anthracene moiety resulting in formation of a rearrangement ion. Moreover, the carbocation prefers to attack the gamma position rather than the alpha or beta position of the anthracene moiety by an electrophilic substitution mechanism. Copyright 2010 American Society for Mass Spectrometry. Published by Elsevier Inc. All rights reserved.

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Year:  2009        PMID： 20044271     DOI： 10.1016/j.jasms.2009.11.004

Source DB:  PubMed          Journal:  J Am Soc Mass Spectrom        ISSN： 1044-0305            Impact factor:   3.109


  22 in total

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