Carbene-catalyzed chirality-controlled site-selective acylation of saccharides
Abstract Acylation stands as a fundamental process in both biological pathways and synthetic chemical reactions, with acylated saccharides and their derivatives holding diverse applications ranging from bioactive agents to synthetic building blocks. A longstanding objective in organic synthesis has...
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| Format: | Article |
| Language: | English |
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Nature Portfolio
2025-01-01
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| Series: | Nature Communications |
| Online Access: | https://doi.org/10.1038/s41467-024-55282-y |
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| author | Ying-Guo Liu Zetao Zhong Yuyang Tang Hongling Wang Sai Vikrama Chaitanya Vummaleti Xi Peng Peng Peng Xinglong Zhang Yonggui Robin Chi |
| author_facet | Ying-Guo Liu Zetao Zhong Yuyang Tang Hongling Wang Sai Vikrama Chaitanya Vummaleti Xi Peng Peng Peng Xinglong Zhang Yonggui Robin Chi |
| author_sort | Ying-Guo Liu |
| collection | DOAJ |
| description | Abstract Acylation stands as a fundamental process in both biological pathways and synthetic chemical reactions, with acylated saccharides and their derivatives holding diverse applications ranging from bioactive agents to synthetic building blocks. A longstanding objective in organic synthesis has been the site-selective acylation of saccharides without extensive pre-protection of alcohol units. In this study, we demonstrate that by simply altering the chirality of N-heterocyclic carbene (NHC) organic catalysts, the site-selectivity of saccharide acylation reactions can be effectively modulated. Our investigation reveals that this intriguing selectivity shift stems from a combination of factors, including chirality match/mismatch and inter- / intramolecular hydrogen bonding between the NHC catalyst and saccharide substrates. These findings provide valuable insights into catalyst design and reaction engineering, highlighting potential applications in glycoside analysis, such as fluorescent labelling, α/β identification, orthogonal reactions, and selective late-stage modifications. |
| format | Article |
| id | doaj-art-e17cf23ec4b84d4badb7be62cdd1f67a |
| institution | Kabale University |
| issn | 2041-1723 |
| language | English |
| publishDate | 2025-01-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Nature Communications |
| spelling | doaj-art-e17cf23ec4b84d4badb7be62cdd1f67a2025-01-05T12:39:30ZengNature PortfolioNature Communications2041-17232025-01-0116111010.1038/s41467-024-55282-yCarbene-catalyzed chirality-controlled site-selective acylation of saccharidesYing-Guo Liu0Zetao Zhong1Yuyang Tang2Hongling Wang3Sai Vikrama Chaitanya Vummaleti4Xi Peng5Peng Peng6Xinglong Zhang7Yonggui Robin Chi8Division of Molecular Catalysis and Synthesis, Henan Institute of Advanced Technology, Zhengzhou UniversityDivision of Molecular Catalysis and Synthesis, Henan Institute of Advanced Technology, Zhengzhou UniversityDivision of Molecular Catalysis and Synthesis, Henan Institute of Advanced Technology, Zhengzhou UniversitySchool of Chemistry, Chemical Engineering, and Biotechnology, Nanyang Technological UniversityDepartment of Chemistry, The Chinese University of Hong Kong, ShatinDivision of Molecular Catalysis and Synthesis, Henan Institute of Advanced Technology, Zhengzhou UniversityNational Glycoengineering Research Centre, Shandong Key Laboratory of Carbohydrate Chemistry and Glycobiology, NMPA Key Laboratory for Quality Research and Evaluation of Carbohydrate Based Medicine, Shandong UniversityDepartment of Chemistry, The Chinese University of Hong Kong, ShatinSchool of Chemistry, Chemical Engineering, and Biotechnology, Nanyang Technological UniversityAbstract Acylation stands as a fundamental process in both biological pathways and synthetic chemical reactions, with acylated saccharides and their derivatives holding diverse applications ranging from bioactive agents to synthetic building blocks. A longstanding objective in organic synthesis has been the site-selective acylation of saccharides without extensive pre-protection of alcohol units. In this study, we demonstrate that by simply altering the chirality of N-heterocyclic carbene (NHC) organic catalysts, the site-selectivity of saccharide acylation reactions can be effectively modulated. Our investigation reveals that this intriguing selectivity shift stems from a combination of factors, including chirality match/mismatch and inter- / intramolecular hydrogen bonding between the NHC catalyst and saccharide substrates. These findings provide valuable insights into catalyst design and reaction engineering, highlighting potential applications in glycoside analysis, such as fluorescent labelling, α/β identification, orthogonal reactions, and selective late-stage modifications.https://doi.org/10.1038/s41467-024-55282-y |
| spellingShingle | Ying-Guo Liu Zetao Zhong Yuyang Tang Hongling Wang Sai Vikrama Chaitanya Vummaleti Xi Peng Peng Peng Xinglong Zhang Yonggui Robin Chi Carbene-catalyzed chirality-controlled site-selective acylation of saccharides Nature Communications |
| title | Carbene-catalyzed chirality-controlled site-selective acylation of saccharides |
| title_full | Carbene-catalyzed chirality-controlled site-selective acylation of saccharides |
| title_fullStr | Carbene-catalyzed chirality-controlled site-selective acylation of saccharides |
| title_full_unstemmed | Carbene-catalyzed chirality-controlled site-selective acylation of saccharides |
| title_short | Carbene-catalyzed chirality-controlled site-selective acylation of saccharides |
| title_sort | carbene catalyzed chirality controlled site selective acylation of saccharides |
| url | https://doi.org/10.1038/s41467-024-55282-y |
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