Efficient and versatile formation of glycosidic bonds via catalytic strain-release glycosylation with glycosyl ortho-2,2-dimethoxycarbonylcyclopropylbenzoate donors
Catalytic glycosylation is a vital transformation in synthetic carbohydrate chemistry due to its ability to expediate the large-scale oligosaccharide synthesis for glycobiology studies with the consumption of minimal amounts of promoters. Herein we introduce a facile and efficient catalytic glycosyl...
| Main Authors: | , , , , |
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| Format: | Journal Article |
| Language: | English |
| Published: |
2023
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| Online Access: | https://hdl.handle.net/10356/170942 |
| _version_ | 1811680991878578176 |
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| author | Ding, Han Lyu, Jian Zhang, Xiao-Lin Xiao, Xiong Liu, Xue-Wei |
| author2 | School of Chemistry, Chemical Engineering and Biotechnology |
| author_facet | School of Chemistry, Chemical Engineering and Biotechnology Ding, Han Lyu, Jian Zhang, Xiao-Lin Xiao, Xiong Liu, Xue-Wei |
| author_sort | Ding, Han |
| collection | NTU |
| description | Catalytic glycosylation is a vital transformation in synthetic carbohydrate chemistry due to its ability to expediate the large-scale oligosaccharide synthesis for glycobiology studies with the consumption of minimal amounts of promoters. Herein we introduce a facile and efficient catalytic glycosylation employing glycosyl ortho-2,2-dimethoxycarbonylcyclopropylbenzoates (CCBz) promoted by a readily accessible and non-toxic Sc(III) catalyst system. The glycosylation reaction involves a novel activation mode of glycosyl esters driven by the ring-strain release of an intramolecularly incorporated donor-acceptor cyclopropane (DAC). The versatile glycosyl CCBz donor enables highly efficient construction of O-, S-, and N-glycosidic bonds under mild conditions, as exemplified by the convenient preparation of the synthetically challenging chitooligosaccharide derivatives. Of note, a gram-scale synthesis of tetrasaccharide corresponding to Lipid IV with modifiable handles is achieved using the catalytic strain-release glycosylation. These attractive features promise this donor to be the prototype for developing next generation of catalytic glycosylation. |
| first_indexed | 2024-10-01T03:33:51Z |
| format | Journal Article |
| id | ntu-10356/170942 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T03:33:51Z |
| publishDate | 2023 |
| record_format | dspace |
| spelling | ntu-10356/1709422023-10-13T15:31:43Z Efficient and versatile formation of glycosidic bonds via catalytic strain-release glycosylation with glycosyl ortho-2,2-dimethoxycarbonylcyclopropylbenzoate donors Ding, Han Lyu, Jian Zhang, Xiao-Lin Xiao, Xiong Liu, Xue-Wei School of Chemistry, Chemical Engineering and Biotechnology Science::Chemistry Benzoic Acid Derivative Glycosylation Catalytic glycosylation is a vital transformation in synthetic carbohydrate chemistry due to its ability to expediate the large-scale oligosaccharide synthesis for glycobiology studies with the consumption of minimal amounts of promoters. Herein we introduce a facile and efficient catalytic glycosylation employing glycosyl ortho-2,2-dimethoxycarbonylcyclopropylbenzoates (CCBz) promoted by a readily accessible and non-toxic Sc(III) catalyst system. The glycosylation reaction involves a novel activation mode of glycosyl esters driven by the ring-strain release of an intramolecularly incorporated donor-acceptor cyclopropane (DAC). The versatile glycosyl CCBz donor enables highly efficient construction of O-, S-, and N-glycosidic bonds under mild conditions, as exemplified by the convenient preparation of the synthetically challenging chitooligosaccharide derivatives. Of note, a gram-scale synthesis of tetrasaccharide corresponding to Lipid IV with modifiable handles is achieved using the catalytic strain-release glycosylation. These attractive features promise this donor to be the prototype for developing next generation of catalytic glycosylation. Agency for Science, Technology and Research (A*STAR) Ministry of Education (MOE) National Research Foundation (NRF) Published version We thank The National Research Foundation (NRF-CRP22-2019-0002), Ministry of Education (MOE-T2EP30120-0007), and A*STAR (A20E5c0087) from Singapore for the financial support and The National Natural Science Foundation of China (22207092), The Natural Science Basic Research Plan of Shaanxi Province of China (2022JQ-091), and The Fundamental Research Funds for the Central Universities (G2021KY05117) from China for financial support. 2023-10-09T05:06:09Z 2023-10-09T05:06:09Z 2023 Journal Article Ding, H., Lyu, J., Zhang, X., Xiao, X. & Liu, X. (2023). Efficient and versatile formation of glycosidic bonds via catalytic strain-release glycosylation with glycosyl ortho-2,2-dimethoxycarbonylcyclopropylbenzoate donors. Nature Communications, 14(1), 4010-. https://dx.doi.org/10.1038/s41467-023-39619-7 2041-1723 https://hdl.handle.net/10356/170942 10.1038/s41467-023-39619-7 37419914 2-s2.0-85164136490 1 14 4010 en NRF-CRP22-2019-0002 MOE-T2EP30120-0007 A20E5c0087 Nature Communications © The Author(s) 2023. Open Access. This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/. application/pdf |
| spellingShingle | Science::Chemistry Benzoic Acid Derivative Glycosylation Ding, Han Lyu, Jian Zhang, Xiao-Lin Xiao, Xiong Liu, Xue-Wei Efficient and versatile formation of glycosidic bonds via catalytic strain-release glycosylation with glycosyl ortho-2,2-dimethoxycarbonylcyclopropylbenzoate donors |
| title | Efficient and versatile formation of glycosidic bonds via catalytic strain-release glycosylation with glycosyl ortho-2,2-dimethoxycarbonylcyclopropylbenzoate donors |
| title_full | Efficient and versatile formation of glycosidic bonds via catalytic strain-release glycosylation with glycosyl ortho-2,2-dimethoxycarbonylcyclopropylbenzoate donors |
| title_fullStr | Efficient and versatile formation of glycosidic bonds via catalytic strain-release glycosylation with glycosyl ortho-2,2-dimethoxycarbonylcyclopropylbenzoate donors |
| title_full_unstemmed | Efficient and versatile formation of glycosidic bonds via catalytic strain-release glycosylation with glycosyl ortho-2,2-dimethoxycarbonylcyclopropylbenzoate donors |
| title_short | Efficient and versatile formation of glycosidic bonds via catalytic strain-release glycosylation with glycosyl ortho-2,2-dimethoxycarbonylcyclopropylbenzoate donors |
| title_sort | efficient and versatile formation of glycosidic bonds via catalytic strain release glycosylation with glycosyl ortho 2 2 dimethoxycarbonylcyclopropylbenzoate donors |
| topic | Science::Chemistry Benzoic Acid Derivative Glycosylation |
| url | https://hdl.handle.net/10356/170942 |
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