Thiol-specific silicon-containing conjugating reagent: β-silyl alkynyl carbonyl compounds
Site-specific modification of thiol-containing biomolecules has been recognized as a versatile and powerful strategy for probing our biological systems and discovering novel therapeutics. The addition of lipophilic silicon moiety opens up new avenues for multi-disciplinary research with broad applic...
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sg-ntu-dr.10356-1716582023-11-03T15:31:47Z Thiol-specific silicon-containing conjugating reagent: β-silyl alkynyl carbonyl compounds Teng, Shenghan Zhang, Zhenguo Li, Bohan Li, Lanyang Tan, Melinda Chor Li Jia, Zhenhua Loh, Teck-Peng School of Chemistry, Chemical Engineering and Biotechnology Science::Chemistry Alkynyl Carbonyl Reagents Biocompatibility Site-specific modification of thiol-containing biomolecules has been recognized as a versatile and powerful strategy for probing our biological systems and discovering novel therapeutics. The addition of lipophilic silicon moiety opens up new avenues for multi-disciplinary research with broad applications in both the medicinal and material sciences. However, adhering to the strict biocompatibility requirements, and achieving the introduction of labile silicon handle and high chemo-selectivity have been formidable. In this paper, we report silicon-based conjugating reagents including β-trialkylsilyl and silyl ether-tethered alkynones that selectively react with thiols under physiological conditions. The pH-neutral, metal-free and additive-free reaction yields stable products with broad substrate compatibility and full retention of silicon handles in most cases. Besides simple aliphatic and aromatic thiols, this approach is applicable in the labeling of thiols present in proteins, sugars and payloads, thereby expanding the toolbox of thiol conjugation. Agency for Science, Technology and Research (A*STAR) Ministry of Education (MOE) Nanyang Technological University Submitted/Accepted version We gratefully acknowledge the financial support from Distinguished University Professor grant (Nanyang Technological University), AcRF Tier1 grant from the Ministry of Education of Singapore (RT14/20) and the Agency for Science, Technology and Research (A*STAR) under its MTC Individual Research Grant (M21K2c0114) and RIE2025 MTC Programmatic Fund (M22K9b0049) for TPL. We also thank “High-end Talents” start up grant (Y0720327K13) from Fujian Normal University for ST. 2023-11-03T01:28:13Z 2023-11-03T01:28:13Z 2023 Journal Article Teng, S., Zhang, Z., Li, B., Li, L., Tan, M. C. L., Jia, Z. & Loh, T. (2023). Thiol-specific silicon-containing conjugating reagent: β-silyl alkynyl carbonyl compounds. Angewandte Chemie International Edition, 62(45), e202311906-. https://dx.doi.org/10.1002/anie.202311906 1433-7851 https://hdl.handle.net/10356/171658 10.1002/anie.202311906 37721855 2-s2.0-85172917869 45 62 e202311906 en RT14/20 M21K2c0114 M22K9b0049 Angewandte Chemie International Edition © 2023 Wiley-VCHGmbH. All rights reserved. This article may be downloaded for personal use only. Any other use requires prior permission of the copyright holder. The Version of Record is available online at http://doi.org/10.1002/anie.202311906. application/pdf |
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Science::Chemistry Alkynyl Carbonyl Reagents Biocompatibility Teng, Shenghan Zhang, Zhenguo Li, Bohan Li, Lanyang Tan, Melinda Chor Li Jia, Zhenhua Loh, Teck-Peng Thiol-specific silicon-containing conjugating reagent: β-silyl alkynyl carbonyl compounds |
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Site-specific modification of thiol-containing biomolecules has been recognized as a versatile and powerful strategy for probing our biological systems and discovering novel therapeutics. The addition of lipophilic silicon moiety opens up new avenues for multi-disciplinary research with broad applications in both the medicinal and material sciences. However, adhering to the strict biocompatibility requirements, and achieving the introduction of labile silicon handle and high chemo-selectivity have been formidable. In this paper, we report silicon-based conjugating reagents including β-trialkylsilyl and silyl ether-tethered alkynones that selectively react with thiols under physiological conditions. The pH-neutral, metal-free and additive-free reaction yields stable products with broad substrate compatibility and full retention of silicon handles in most cases. Besides simple aliphatic and aromatic thiols, this approach is applicable in the labeling of thiols present in proteins, sugars and payloads, thereby expanding the toolbox of thiol conjugation. |
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School of Chemistry, Chemical Engineering and Biotechnology |
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School of Chemistry, Chemical Engineering and Biotechnology Teng, Shenghan Zhang, Zhenguo Li, Bohan Li, Lanyang Tan, Melinda Chor Li Jia, Zhenhua Loh, Teck-Peng |
format |
Article |
author |
Teng, Shenghan Zhang, Zhenguo Li, Bohan Li, Lanyang Tan, Melinda Chor Li Jia, Zhenhua Loh, Teck-Peng |
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Teng, Shenghan |
title |
Thiol-specific silicon-containing conjugating reagent: β-silyl alkynyl carbonyl compounds |
title_short |
Thiol-specific silicon-containing conjugating reagent: β-silyl alkynyl carbonyl compounds |
title_full |
Thiol-specific silicon-containing conjugating reagent: β-silyl alkynyl carbonyl compounds |
title_fullStr |
Thiol-specific silicon-containing conjugating reagent: β-silyl alkynyl carbonyl compounds |
title_full_unstemmed |
Thiol-specific silicon-containing conjugating reagent: β-silyl alkynyl carbonyl compounds |
title_sort |
thiol-specific silicon-containing conjugating reagent: β-silyl alkynyl carbonyl compounds |
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2023 |
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https://hdl.handle.net/10356/171658 |
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