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

Jason   J.   Chruma; Sung-Ju      Moon; William   E.   Sanford Jr.

doi:10.2174/157017809788681428

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

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Letters in Organic Chemistry

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

Volume: 6 Issue: 5

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

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

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.

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Chruma J. Jason, Moon Sung-Ju and Sanford Jr. E. William, Azaphilone α-Bromoacetates (AzαBs): Fluorescent Linchpin Reagents for the Inter- and Intramolecular Cross-Linkage of Primary Amines to Thiols, Letters in Organic Chemistry 2009; 6 (5) . https://dx.doi.org/10.2174/157017809788681428