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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| Korporacja: | |
| Kolejni autorzy: | , , , , |
| Streszczenie: | 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 |
| Język: | angielski |
| Wydane: |
2015
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| Hasła przedmiotowe: | |
| Dostęp online: | http://dx.doi.org/10.1039/C4OB01350F |
| Format: | Elektroniczne Rozdział |
| KOHA link: | https://koha.lib.tpu.ru/cgi-bin/koha/opac-detail.pl?biblionumber=643209 |
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| 200 | 1 | |a Water-soluble NHC-Cu catalysts: applications in click chemistry, bioconjugation and mechanistic analysis |f V. H. Velazquez [et al.] | |
| 203 | |a Text |c electronic | ||
| 300 | |a Title screen | ||
| 320 | |a [References: p. 9356 (30 tit.)] | ||
| 330 | |a 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. | ||
| 333 | |a Режим доступа: по договору с организацией-держателем ресурса | ||
| 461 | |t Organic and Biomolecular Chemistry | ||
| 463 | |t Vol. 12, iss. 46 |v [P. 9350-9356] |d 2015 | ||
| 610 | 1 | |a электронный ресурс | |
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| 701 | 1 | |a Garcia |b Ya. R. |g Yara Ruiz | |
| 701 | 1 | |a Vandichel |b M. |g Matthias | |
| 701 | 1 | |a Madder |b A. |g Annemieke | |
| 701 | 1 | |a Verpoort |b F. V. K. |c Chemical Engineer |c Professor of Tomsk Polytechnic University, doctor of chemical Sciences |f 1963- |g Frensis Valter Kornelius |3 (RuTPU)RU\TPU\pers\35059 |9 18334 | |
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