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-Bioti...

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Bibliographic Details
Published in:Amino acids 2023-12, Vol.55 (12), p.1981-1989
Main Authors: Maurya, Shakti K., Tripathi, Abhishek, Karuthapandi, Selvakumar, Singh, Harkesh B.
Format: Article
Language:English
Subjects:
Amino acids
Analytical Chemistry
Antioxidants
Antioxidants - chemistry
Biochemical Engineering
Biochemistry
Biomedical and Life Sciences
Biomolecules
Biotechnology
Biotin
biphenyl
Conjugation
Enzymatic activity
enzyme activity
Enzymes
Glutathione
Glutathione - chemistry
Glutathione Peroxidase
Hydrogen peroxide
Life Sciences
Lipoic acid
Magnetic resonance spectroscopy
Materials science
Neurobiology
NMR spectroscopy
nuclear magnetic resonance spectroscopy
Organoselenium Compounds - chemistry
Original Article
Peptide synthesis
Peptides
Peroxidase
Proteomics
Reductases
Scientific imaging
Selenium
Solid phases
Synthesis
Thioctic Acid - chemistry
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Summary: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 ( 1 H, 13 C, 77 Se) and 2D ( 1 H- 1 H COSY and 1 H- 13 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 (Ph 2 Se 2 ), L-selenocystine (SeC), biotin, lipoic acid, and ebselen.
ISSN:0939-4451
1438-2199
DOI:10.1007/s00726-023-03348-4