@article{nuruzzaman_colella_uzoewulu_meo_gross_ishizawa_sana_zhang_hoff_medlock_et al._2024, title={Hexafluoroisopropanol as a Bioconjugation Medium of Ultrafast, Tryptophan-Selective Catalysis}, volume={2}, ISSN={["1520-5126"]}, DOI={10.1021/jacs.3c13447}, abstractNote={The past decade has seen a remarkable growth in the number of bioconjugation techniques in chemistry, biology, material science, and biomedical fields. A core design element in bioconjugation technology is a chemical reaction that can form a covalent bond between the protein of interest and the labeling reagent. Achieving chemoselective protein bioconjugation in aqueous media is challenging, especially for generally less reactive amino acid residues, such as tryptophan. We present here the development of tryptophan-selective bioconjugation methods through ultrafast Lewis acid-catalyzed reactions in hexafluoroisopropanol (HFIP). Structure-reactivity relationship studies have revealed a combination of thiophene and ethanol moieties to give a suitable labeling reagent for this bioconjugation process, which enables modification of peptides and proteins in an extremely rapid reaction unencumbered by noticeable side reactions. The capability of the labeling method also facilitated radiofluorination application as well as antibody functionalization. Enhancement of an α-helix by HFIP leads to its compatibility with a certain protein, and this report also demonstrates a further stabilization strategy achieved by the addition of an ionic liquid to the HFIP medium. The nonaqueous bioconjugation approaches allow access to numerous chemical reactions that are unavailable in traditional aqueous processes and will further advance the chemistry of proteins.}, journal={JOURNAL OF THE AMERICAN CHEMICAL SOCIETY}, author={Nuruzzaman, Mohammad and Colella, Brandon M. and Uzoewulu, Chiamaka P. and Meo, Alissa E. and Gross, Elizabeth J. and Ishizawa, Seiya and Sana, Sravani and Zhang, He and Hoff, Meredith E. and Medlock, Bryce T. W. and et al.}, year={2024}, month={Feb} }
 @article{ishizawa_tumurkhuu_gross_ohata_2022, title={Site-specific DNA functionalization through the tetrazene-forming reaction in ionic liquids}, volume={1}, ISSN={["2041-6539"]}, url={https://doi.org/10.1039/D1SC05204G}, DOI={10.1039/D1SC05204G}, abstractNote={Site-specific chemical modification of unprotected DNAs through a phosphine-mediated amine–azide coupling reaction in ionic liquid.}, journal={CHEMICAL SCIENCE}, publisher={Royal Society of Chemistry (RSC)}, author={Ishizawa, Seiya and Tumurkhuu, Munkhtuya and Gross, Elizabeth J. and Ohata, Jun}, year={2022}, month={Jan} }
 @article{ishizawa_tumurkhuu_gross_ohata_2022, title={Site-specific DNA functionalization through the tetrazene-forming reaction in ionic liquids (vol 13, pg 1780, 2022)}, volume={13}, ISSN={["2041-6539"]}, DOI={10.1039/d2sc90102a}, abstractNote={Correction for ‘Site-specific DNA functionalization through the tetrazene-forming reaction in ionic liquids’ by Seiya Ishizawa et al., Chem. Sci., 2022, 13, 1780–1788, https://doi.org/10.1039/d1sc05204g.}, number={22}, journal={CHEMICAL SCIENCE}, author={Ishizawa, Seiya and Tumurkhuu, Munkhtuya and Gross, Elizabeth J. and Ohata, Jun}, year={2022}, month={Jun}, pages={6749–6751} }
 @article{el-shaffey_gross_hall_ohata_2021, title={An Ionic Liquid Medium Enables Development of a Phosphine-Mediated Amine-Azide Bioconjugation Method}, volume={143}, ISSN={["1520-5126"]}, url={https://doi.org/10.1021/jacs.1c06092}, DOI={10.1021/jacs.1c06092}, abstractNote={While a diverse set of design strategies have produced various chemical tools for biomolecule labeling in aqueous media, the development of nonaqueous, biomolecule-compatible media for bioconjugation has significantly lagged behind. In this report, we demonstrate that an aprotic ionic liquid serves as a novel reaction solvent for protein bioconjugation without noticeable loss of the biomolecule functions. The ionic liquid bioconjugation approach led to discovery of a novel triphenylphosphine-mediated amine-azide coupling reaction that forges a stable tetrazene linkage on unprotected peptides and proteins. This strategy of using untraditional media would provide untapped opportunities for expanding the scope of chemical approaches for bioconjugation.}, number={33}, journal={JOURNAL OF THE AMERICAN CHEMICAL SOCIETY}, publisher={American Chemical Society (ACS)}, author={El-Shaffey, Hisham M. and Gross, Elizabeth J. and Hall, Yvonne D. and Ohata, Jun}, year={2021}, month={Aug}, pages={12974–12979} }