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Bioconjugation by native chemical tagging of C-H bonds.

ABSTRACT: A general C-H functionalization method for the tagging of natural products and pharmaceuticals is described. An azide-containing sulfinate reagent allows the appendage of azidoalkyl chains onto heteroaromatics, the product of which can then be attached to a monoclonal antibody by a "click" reaction. This strategy expands the breadth of bioactive small molecules that can be linked to macromolecules in a manner that is beyond the scope of existing methods in bioconjugation to permit tagging of the "seemingly untaggable".

SUBMITTER: Zhou Q

PROVIDER: S-EPMC3812917 | biostudies-literature | 2013 Sep

REPOSITORIES: biostudies-literature

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Bioconjugation by native chemical tagging of C-H bonds.

Zhou Qianghui Q Gui Jinghan J Pan Chung-Mao CM Albone Earl E Cheng Xin X Suh Edward M EM Grasso Luigi L Ishihara Yoshihiro Y Baran Phil S PS

Journal of the American Chemical Society 20130822 35

A general C-H functionalization method for the tagging of natural products and pharmaceuticals is described. An azide-containing sulfinate reagent allows the appendage of azidoalkyl chains onto heteroaromatics, the product of which can then be attached to a monoclonal antibody by a "click" reaction. This strategy expands the breadth of bioactive small molecules that can be linked to macromolecules in a manner that is beyond the scope of existing methods in bioconjugation to permit tagging of the ...[more]

PMID: 23957305

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