Department of Chemistry, Indian Institute of Technology Bombay, Mumbai, 400076, India.
Department of Chemistry, School of Advanced Sciences, VIT-AP University, Amaravati, AP, 522241, India.
Amino Acids. 2023 Dec;55(12):1981-1989. doi: 10.1007/s00726-023-03348-4. Epub 2023 Nov 16.
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 (H, C, Se) and 2D (H-H COSY and H-C 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 (PhSe), L-selenocystine (SeC), biotin, lipoic acid, and ebselen.
活性生物分子的缀合提供了对其生物反应性的深入了解，从而在生物技术和材料科学中有许多应用。在此，我们报告了脂酸（通用抗氧化剂）和生物素（维生素 H）的 L-硒代半胱氨酸（SeC）生物缀合物。使用固相肽合成（SPPS）方法合成了 SeC-生物素（1）和 SeC-脂酸（2）的 SeC 生物缀合物，并通过多核 1D（H、C、Se）和 2D（H-H COSY 和 H-C TOCSY）NMR 光谱、ESI-MS 光谱和 RP-HPLC 进行了表征。通过偶联还原酶测定法研究了 SeC-生物缀合物 1 和 2 的 GPx 样酶模拟活性，用于催化过氧化氢还原为水。与二苯并硒（PhSe）、L-硒代半胱氨酸（SeC）、生物素、脂酸和艾地苯相比，两种新型生物缀合物 SeC-生物素（1）和 SeC-脂酸（2）的 GPx 样酶活性均显著增强。
