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Development and Optimization of Glaser–Hay Bioconjugations
Author(s) -
Lampkowski Jessica S.,
Villa Jordan K.,
Young Travis S.,
Young Douglas D.
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201502676
Subject(s) - bioorthogonal chemistry , chemistry , amino acid , aqueous solution , molecule , combinatorial chemistry , coupling reaction , small molecule , hay , translation (biology) , organic chemistry , biochemistry , biology , click chemistry , catalysis , messenger rna , gene , agronomy
Abstract The prevalence of bioconjugates in the biomedical sciences necessitates the development of novel mechanisms to facilitate their preparation. Towards this end, the translation of the Glaser–Hay coupling to an aqueous environment is examined, and its potential as a bioorthogonal conjugation reaction is demonstrated. This optimized, novel, and aqueous Glaser–Hay reaction is applied towards the development of bioconjugates utilizing protein expressed with an alkynyl unnatural amino acid. Unnatural amino acid technology provides a degree of bioorthognality and specificity not feasible with other methods. Moreover, the scope of the reaction is demonstrated through protein–small molecule couplings, small‐molecule–solid‐support couplings, and protein–solid‐support immobilizations.