Shakti K. Maurya, Abhishek Tripathi, Selvakumar Karuthapandi, Harkesh B. Singh
{"title":"硒半胱氨酸(SeC)生物素和硫辛酸偶联物的合成及谷胱甘肽过氧化物酶样活性研究。","authors":"Shakti K. Maurya, Abhishek Tripathi, Selvakumar Karuthapandi, Harkesh B. Singh","doi":"10.1007/s00726-023-03348-4","DOIUrl":null,"url":null,"abstract":"<div><p>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 (<b>1</b>) and SeC-Lipoic acid (<b>2</b>) were synthesized using solid phase peptide synthesis (SPPS) method and were characterized by multinuclear 1D (<sup>1</sup>H, <sup>13</sup>C, <sup>77</sup>Se) and 2D (<sup>1</sup>H-<sup>1</sup>H COSY and <sup>1</sup>H-<sup>13</sup>C TOCSY) NMR spectroscopy, ESI–MS spectrometry, and RP-HPLC. The GPx-like enzyme mimicking activity of the SeC-bioconjugates <b>1</b> and <b>2</b> has been investigated through the coupled reductase assay method for the catalytic reductions of hydrogen peroxide into water<sub>.</sub> A significant enhancement in GPx-like enzymatic activity was observed for both novel bioconjugates SeC-Biotin (<b>1</b>) and SeC-Lipoic acid (<b>2</b>) as compared to diphenyl diselenide (Ph<sub>2</sub>Se<sub>2</sub>), L-selenocystine (SeC), biotin, lipoic acid, and ebselen.</p></div>","PeriodicalId":7810,"journal":{"name":"Amino Acids","volume":"55 12","pages":"1981 - 1989"},"PeriodicalIF":3.0000,"publicationDate":"2023-11-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Synthesis and glutathione peroxidase (GPx)-like activity of selenocystine (SeC) bioconjugates of biotin and lipoic acid\",\"authors\":\"Shakti K. Maurya, Abhishek Tripathi, Selvakumar Karuthapandi, Harkesh B. Singh\",\"doi\":\"10.1007/s00726-023-03348-4\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>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 (<b>1</b>) and SeC-Lipoic acid (<b>2</b>) were synthesized using solid phase peptide synthesis (SPPS) method and were characterized by multinuclear 1D (<sup>1</sup>H, <sup>13</sup>C, <sup>77</sup>Se) and 2D (<sup>1</sup>H-<sup>1</sup>H COSY and <sup>1</sup>H-<sup>13</sup>C TOCSY) NMR spectroscopy, ESI–MS spectrometry, and RP-HPLC. The GPx-like enzyme mimicking activity of the SeC-bioconjugates <b>1</b> and <b>2</b> has been investigated through the coupled reductase assay method for the catalytic reductions of hydrogen peroxide into water<sub>.</sub> A significant enhancement in GPx-like enzymatic activity was observed for both novel bioconjugates SeC-Biotin (<b>1</b>) and SeC-Lipoic acid (<b>2</b>) as compared to diphenyl diselenide (Ph<sub>2</sub>Se<sub>2</sub>), L-selenocystine (SeC), biotin, lipoic acid, and ebselen.</p></div>\",\"PeriodicalId\":7810,\"journal\":{\"name\":\"Amino Acids\",\"volume\":\"55 12\",\"pages\":\"1981 - 1989\"},\"PeriodicalIF\":3.0000,\"publicationDate\":\"2023-11-16\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Amino Acids\",\"FirstCategoryId\":\"99\",\"ListUrlMain\":\"https://link.springer.com/article/10.1007/s00726-023-03348-4\",\"RegionNum\":3,\"RegionCategory\":\"生物学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"BIOCHEMISTRY & MOLECULAR BIOLOGY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Amino Acids","FirstCategoryId":"99","ListUrlMain":"https://link.springer.com/article/10.1007/s00726-023-03348-4","RegionNum":3,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"BIOCHEMISTRY & MOLECULAR BIOLOGY","Score":null,"Total":0}
Synthesis and glutathione peroxidase (GPx)-like activity of selenocystine (SeC) bioconjugates of biotin and lipoic acid
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.
期刊介绍:
Amino Acids publishes contributions from all fields of amino acid and protein research: analysis, separation, synthesis, biosynthesis, cross linking amino acids, racemization/enantiomers, modification of amino acids as phosphorylation, methylation, acetylation, glycosylation and nonenzymatic glycosylation, new roles for amino acids in physiology and pathophysiology, biology, amino acid analogues and derivatives, polyamines, radiated amino acids, peptides, stable isotopes and isotopes of amino acids. Applications in medicine, food chemistry, nutrition, gastroenterology, nephrology, neurochemistry, pharmacology, excitatory amino acids are just some of the topics covered. Fields of interest include: Biochemistry, food chemistry, nutrition, neurology, psychiatry, pharmacology, nephrology, gastroenterology, microbiology