A novel rearrangement of fluorescent human thymidylate synthase inhibitor analogues in ESI tandem mass spectrometry View Full Text


Ontology type: schema:ScholarlyArticle      Open Access: True


Article Info

DATE

2010-03

AUTHORS

Yi Chen, 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. More... »

PAGES

403-410

Identifiers

URI

http://scigraph.springernature.com/pub.10.1016/j.jasms.2009.11.004

DOI

http://dx.doi.org/10.1016/j.jasms.2009.11.004

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1031196915

PUBMED

https://www.ncbi.nlm.nih.gov/pubmed/20044271


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