Water-soluble NHC-Cu catalysts: applications in click chemistry, bioconjugation and mechanistic analysis
| Parent link: | Organic and Biomolecular Chemistry Vol. 12, iss. 46.— 2015.— [P. 9350-9356] |
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| مؤلف مشترك: | |
| مؤلفون آخرون: | , , , , |
| الملخص: | Title screen Copper(I)-catalyzed 1,3-dipolar cycloaddition of azides and terminal alkynes (CuAAC), better known as“click” reaction, has triggered the use of 1,2,3-triazoles in bioconjugation, drug discovery, materialsscience and combinatorial chemistry. Here we report a new series of water-soluble catalysts based onN-heterocyclic carbene (NHC)-Cu complexes which are additionally functionalized with a sulfonategroup. The complexes show superior activity towards CuAAC reactions and display a high versatility,enabling the production of triazoles with different substitution patterns. Additionally, successful applicationof these complexes in bioconjugation using unprotected peptides acting as DNA binding domainswas achieved for the first time. Mechanistic insight into the reaction mechanism is obtained by means ofstate-of-the-art first principles calculations. Режим доступа: по договору с организацией-держателем ресурса |
| منشور في: |
2015
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| الموضوعات: | |
| الوصول للمادة أونلاين: | http://dx.doi.org/10.1039/C4OB01350F |
| التنسيق: | الكتروني فصل الكتاب |
| KOHA link: | https://koha.lib.tpu.ru/cgi-bin/koha/opac-detail.pl?biblionumber=643209 |
| الملخص: | Title screen Copper(I)-catalyzed 1,3-dipolar cycloaddition of azides and terminal alkynes (CuAAC), better known as“click” reaction, has triggered the use of 1,2,3-triazoles in bioconjugation, drug discovery, materialsscience and combinatorial chemistry. Here we report a new series of water-soluble catalysts based onN-heterocyclic carbene (NHC)-Cu complexes which are additionally functionalized with a sulfonategroup. The complexes show superior activity towards CuAAC reactions and display a high versatility,enabling the production of triazoles with different substitution patterns. Additionally, successful applicationof these complexes in bioconjugation using unprotected peptides acting as DNA binding domainswas achieved for the first time. Mechanistic insight into the reaction mechanism is obtained by means ofstate-of-the-art first principles calculations. Режим доступа: по договору с организацией-держателем ресурса |
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| DOI: | 10.1039/C4OB01350F |