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Letters in Organic Chemistry

Author(s): Jason J. Chruma, Sung-Ju Moon and William E. Sanford Jr.

DOI: 10.2174/157017809788681428

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Azaphilone α-Bromoacetates (AzαBs): Fluorescent Linchpin Reagents for the Inter- and Intramolecular Cross-Linkage of Primary Amines to Thiols

Page: [367 - 371] Pages: 5

  • * (Excluding Mailing and Handling)

Abstract

α-Bromoacetate esters of the azaphilone isochromene-6,8-dione core exhibit a pH-dependent orthogonal reactivity allowing for the one-pot cross-linkage of primary amines to thiols in an inter- or intramolecular fashion to afford fluorescent products. This represents a new potential strategy for bioconjugate chemistry.

Keywords: Azaphilones, bioconjugation, orthogonal reactivity, cross-linkage, fluorescent