Development and applications of water-compatible reactions: a journey to be continued
Conspectus:The pursuit of novel and eco-friendly methods in organic synthesis is gaining prominence, with a strong emphasis on green transformations using renewable and sustainable resources. Among these environmentally conscious approaches, water-compatible reactions stand out for their many advant...
| Main Authors: | , |
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| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
| Published: |
2024
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| Online Access: | https://hdl.handle.net/10356/178255 |
| _version_ | 1811687531393056768 |
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| author | Lu, Ming-Zhu Loh, Teck-Peng |
| author2 | School of Chemistry, Chemical Engineering and Biotechnology |
| author_facet | School of Chemistry, Chemical Engineering and Biotechnology Lu, Ming-Zhu Loh, Teck-Peng |
| author_sort | Lu, Ming-Zhu |
| collection | NTU |
| description | Conspectus:The pursuit of novel and eco-friendly methods in organic synthesis is gaining prominence, with a strong emphasis on green transformations using renewable and sustainable resources. Among these environmentally conscious approaches, water-compatible reactions stand out for their many advantages. Water, as a solvent, offers unmatched abundance, cost-efficiency, and environmental compatibility compared to organic solvents. Its use eliminates the need for complex protection and deprotection steps for reactive functional groups in multistep synthesis and enables the use of water-soluble substrates like proteins and carbohydrates. Water-compatible reactions also provide opportunities to combine with enzymes, resulting in chemoenzymatic transformations that can increase efficiency. Additionally, these reactions facilitate site-specific modification and the bioconjugation of biomolecules, leading to bioconjugate therapeutics. Over nearly three decades, our research group has been dedicated to developing innovative water-compatible methodologies and concepts. This Account provides a comprehensive overview of our contributions since 1994. Our central strategy revolves around integrating green chemistry principles into our methods, focusing on (i) developing reactions that can operate under mild conditions, including room temperature, atmospheric pressure, and physiological pH; (ii) designing atom-economical reactions that minimize waste production; (iii) replacing toxic and flammable organic solvents with eco-friendly alternatives like water and ethanol; and (iv) reducing reliance on metals or halogenated compounds in specific reactions. In this Account, we detail our achievements in developing efficient methodologies in aqueous media, highlighting their scope, limitations, asymmetric control, and applications for synthesizing complex molecules and functionalizing peptides and proteins. Mechanistic investigations underlying these developments are also discussed when applicable. Furthermore, we offer insights into the reasoning behind our work and address future opportunities and challenges in this area of research. We hope that this Account will inspire continued interest and foster new breakthroughs. By exploring innovative and broadly applicable strategies that expand the water-compatible synthetic toolbox, we aim to pave the way for the truly green and sustainable synthesis of complex molecules and pharmaceuticals. |
| first_indexed | 2024-10-01T05:17:48Z |
| format | Journal Article |
| id | ntu-10356/178255 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T05:17:48Z |
| publishDate | 2024 |
| record_format | dspace |
| spelling | ntu-10356/1782552024-06-21T15:31:47Z Development and applications of water-compatible reactions: a journey to be continued Lu, Ming-Zhu Loh, Teck-Peng School of Chemistry, Chemical Engineering and Biotechnology Chemistry Green chemistry Organic synthesis Conspectus:The pursuit of novel and eco-friendly methods in organic synthesis is gaining prominence, with a strong emphasis on green transformations using renewable and sustainable resources. Among these environmentally conscious approaches, water-compatible reactions stand out for their many advantages. Water, as a solvent, offers unmatched abundance, cost-efficiency, and environmental compatibility compared to organic solvents. Its use eliminates the need for complex protection and deprotection steps for reactive functional groups in multistep synthesis and enables the use of water-soluble substrates like proteins and carbohydrates. Water-compatible reactions also provide opportunities to combine with enzymes, resulting in chemoenzymatic transformations that can increase efficiency. Additionally, these reactions facilitate site-specific modification and the bioconjugation of biomolecules, leading to bioconjugate therapeutics. Over nearly three decades, our research group has been dedicated to developing innovative water-compatible methodologies and concepts. This Account provides a comprehensive overview of our contributions since 1994. Our central strategy revolves around integrating green chemistry principles into our methods, focusing on (i) developing reactions that can operate under mild conditions, including room temperature, atmospheric pressure, and physiological pH; (ii) designing atom-economical reactions that minimize waste production; (iii) replacing toxic and flammable organic solvents with eco-friendly alternatives like water and ethanol; and (iv) reducing reliance on metals or halogenated compounds in specific reactions. In this Account, we detail our achievements in developing efficient methodologies in aqueous media, highlighting their scope, limitations, asymmetric control, and applications for synthesizing complex molecules and functionalizing peptides and proteins. Mechanistic investigations underlying these developments are also discussed when applicable. Furthermore, we offer insights into the reasoning behind our work and address future opportunities and challenges in this area of research. We hope that this Account will inspire continued interest and foster new breakthroughs. By exploring innovative and broadly applicable strategies that expand the water-compatible synthetic toolbox, we aim to pave the way for the truly green and sustainable synthesis of complex molecules and pharmaceuticals. 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 the National Natural Science Foundation of China (no. 22101095). We also thank the financial support from Distinguished University Professor grant (Nanyang Technological University), AcRF Tier 1 grants from the Ministry of Education of Singapore (RG11/20 and RT14/20), and the Agency for Science, Technology and Research (A*STAR) under its MTC Individual Research Grants (M21K2c0114). 2024-06-10T01:15:34Z 2024-06-10T01:15:34Z 2024 Journal Article Lu, M. & Loh, T. (2024). Development and applications of water-compatible reactions: a journey to be continued. Accounts of Chemical Research, 57(1), 70-92. https://dx.doi.org/10.1021/acs.accounts.3c00555 0001-4842 https://hdl.handle.net/10356/178255 10.1021/acs.accounts.3c00555 38112292 2-s2.0-85180582357 1 57 70 92 en RG11/20 RT14/20 M21K2c0114 Accounts of Chemical Research © 2023 American Chemical Society. 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/10.1021/acs.accounts.3c00555. application/pdf |
| spellingShingle | Chemistry Green chemistry Organic synthesis Lu, Ming-Zhu Loh, Teck-Peng Development and applications of water-compatible reactions: a journey to be continued |
| title | Development and applications of water-compatible reactions: a journey to be continued |
| title_full | Development and applications of water-compatible reactions: a journey to be continued |
| title_fullStr | Development and applications of water-compatible reactions: a journey to be continued |
| title_full_unstemmed | Development and applications of water-compatible reactions: a journey to be continued |
| title_short | Development and applications of water-compatible reactions: a journey to be continued |
| title_sort | development and applications of water compatible reactions a journey to be continued |
| topic | Chemistry Green chemistry Organic synthesis |
| url | https://hdl.handle.net/10356/178255 |
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