Abstract
The conjugation of active biomolecules provides insight into their bioreactivity, leading to many applications in biotechnology and materials science. Herein, we report L-selenocystine (SeC) bioconjugates of lipoic acid (universal antioxidant) and biotin (Vitamin-H). The SeC-bioconjugates, SeC-Biotin (1) and SeC-Lipoic acid (2) were synthesized using solid phase peptide synthesis (SPPS) method and were characterized by multinuclear 1D (1H, 13C, 77Se) and 2D (1H-1H COSY and 1H-13C TOCSY) NMR spectroscopy, ESI–MS spectrometry, and RP-HPLC. The GPx-like enzyme mimicking activity of the SeC-bioconjugates 1 and 2 has been investigated through the coupled reductase assay method for the catalytic reductions of hydrogen peroxide into water. A significant enhancement in GPx-like enzymatic activity was observed for both novel bioconjugates SeC-Biotin (1) and SeC-Lipoic acid (2) as compared to diphenyl diselenide (Ph2Se2), L-selenocystine (SeC), biotin, lipoic acid, and ebselen.
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Acknowledgements
SKM gratefully acknowledges the Indian Institute of Technology, Bombay, for providing JRF and SRF fellowships. SKM and AT recognize the Department of Chemistry and Industrial Research and Consultancy Centre (IRCC), IIT Bombay, for providing the instrument facilities to carry out the present research work. HBS acknowledges the Department of Science and Technology (DST), New Delhi, for the financial support through the J. C. Bose Fellowship.
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SKM designed and performed the experiments. AT has interpreted analytical and GPx-like activity data and prepared the original draft of the manuscript. SK has contributed to the interpretation of data and refined the manuscript. HBS directed the project. All authors participated in manuscript writing and approved the manuscript.
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Maurya, S.K., Tripathi, A., Karuthapandi, S. et al. Synthesis and glutathione peroxidase (GPx)-like activity of selenocystine (SeC) bioconjugates of biotin and lipoic acid. Amino Acids 55, 1981–1989 (2023). https://doi.org/10.1007/s00726-023-03348-4
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DOI: https://doi.org/10.1007/s00726-023-03348-4