Academic Journal
β-Silyl alkynoates: versatile reagents for biocompatible and selective amide bond formation
| العنوان: | β-Silyl alkynoates: versatile reagents for biocompatible and selective amide bond formation |
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| المؤلفون: | Choudhuri, Khokan, Zhang, Zhenguo, Loh, Teck-Peng |
| المساهمون: | School of Chemistry, Chemical Engineering and Biotechnology |
| سنة النشر: | 2024 |
| المجموعة: | DR-NTU (Digital Repository at Nanyang Technological University, Singapore) |
| مصطلحات موضوعية: | Chemistry, Alkynoates, Amide bond formation |
| الوصف: | The study introduces a previously unidentified method for amide bond formation that addresses several limitations of conventional approaches. It uses the β-silyl alkynoate molecule, where the alkynyl group activates the ester for efficient amide formation, while the bulky TIPS (triisopropylsilane) group prevents unwanted 1,4-addition reactions. This approach exhibits high chemoselectivity for amines, making the method compatible with a wide range of substrates, including secondary amines, and targets the specific ε-amino group of lysine among the native amino ester's derivatives. It maintains stereochemistry during amide bond formation and TIPS group removal, allowing a versatile platform for postsynthesis modifications such as click reactions and peptide-drug conjugations. These advancements hold substantial promise for pharmaceutical development and peptide engineering, opening avenues for research applications. ; Agency for Science, Technology and Research (A*STAR) ; Nanyang Technological University ; Published version ; We gratefully acknowledge the financial support from the Distinguished University Professor grant (Nanyang Technological University) and the Agency for Science, Technology and Research (A*STAR) under its MTC Individual Research Grant (M21K2c0114) and RIE2025 MTC Programmatic Fund (M22K9b0049). |
| نوع الوثيقة: | article in journal/newspaper |
| وصف الملف: | application/pdf |
| اللغة: | English |
| Relation: | M21K2c0114; M22K9b0049; Science Advances; https://hdl.handle.net/10356/180454; 38; 10; eadp7544 |
| DOI: | 10.1126/sciadv.adp7544 |
| الاتاحة: | https://hdl.handle.net/10356/180454 https://doi.org/10.1126/sciadv.adp7544 |
| Rights: | © 2024 The Authors, some rights reserved; exclusive licensee American Association for the Advancement of Science. No claim to original U.S. Government Works. Distributed under a Creative Commons Attribution License 4.0 (CC BY). |
| رقم الانضمام: | edsbas.9D3D31C4 |
| قاعدة البيانات: | BASE |
| DOI: | 10.1126/sciadv.adp7544 |
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