The essence of bioconjugation or chemical reactions of biomolecules is organic chemistry where the reactivity/selectivity of substrates and reagents need to examine carefully. Interestingly, unlike typical organic chemistry, screening of reaction media for bioconjugation has not been explored even if such organic chemistry reactions tend to affect by solvents significantly. The Ohata laboratory has been developing nonaqueous bioconjugation methods, termed Bioconjugation In Nonaqueous-Driven Reaction Solvent (BINDRS). With the initial success of the ionic liquid-based bioconjugation methods, the current efforts are focusing on developing new bioconjugation methods using different reaction media. To this end, we began the investigation of reactions of heteroaryl-alcohol compounds in alcohol-based solvents, inspired by the Piancatelli-type reaction.<br/>This study focused on small molecule and peptide substrates to understand the reactivity-structure relationship of the new bioconjugation method. Based on the successful initial screening of tryptophan-containing peptides, amino acid tryptophan was employed as a model substrate to reveal the chemical structure of the bioconjugation product using NMR and LCMS. To pin down the reaction site of the labeling reagents, I have synthesized a series of variants of heteroaryl-alcohols by using borohydride reduction of the corresponding ketone. Currently, the effects of electron-donating and -withdrawing groups on the heteroarene moiety have been investigated, and this project will be translated to larger biomolecules (i.e. proteins) with the optimized chemical labeling reagents.

Development of indole-selective bioconjugation methods

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