Azidoisocyanides, New Bifunctional Reagents for Multicomponent Reactions and Biomolecule Modifications
The synthetic capabilities of chiral α,β-azidoisocyanides were systematically reviewed. The potential of using them as bifunctional building blocks for multicomponent Passerini and Ugi reactions and also for Cu(I)-catalyzed [3+2]-cycloaddition to form 1,2,3-triazoles was demonstrated. The bifunction...
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| Published in | Chemistry of natural compounds Vol. 50; no. 2; pp. 197 - 213 |
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| Main Authors | , |
| Format | Journal Article |
| Language | English |
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Boston
Springer-Verlag
01.05.2014
Springer US Springer |
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| Abstract | The synthetic capabilities of chiral α,β-azidoisocyanides were systematically reviewed. The potential of using them as bifunctional building blocks for multicomponent Passerini and Ugi reactions and also for Cu(I)-catalyzed [3+2]-cycloaddition to form 1,2,3-triazoles was demonstrated. The bifunctional nature of these compounds enabled the development of a methodology for preparing peptides containing an azide group and conjugating them subsequently with various biologically active compounds containing an ethynyl group for targeted modification of biomolecules. |
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| AbstractList | The synthetic capabilities of chiral
α
,
β
-azidoisocyanides were systematically reviewed. The potential of using them as bifunctional building blocks for multicomponent Passerini and Ugi reactions and also for Cu(I)-catalyzed [3+2]-cycloaddition to form 1,2,3-triazoles was demonstrated. The bifunctional nature of these compounds enabled the development of a methodology for preparing peptides containing an azide group and conjugating them subsequently with various biologically active compounds containing an ethynyl group for targeted modification of biomolecules. The synthetic capabilities of chiral α,β-azidoisocyanides were systematically reviewed. The potential of using them as bifunctional building blocks for multicomponent Passerini and Ugi reactions and also for Cu(I)-catalyzed [3+2]-cycloaddition to form 1,2,3-triazoles was demonstrated. The bifunctional nature of these compounds enabled the development of a methodology for preparing peptides containing an azide group and conjugating them subsequently with various biologically active compounds containing an ethynyl group for targeted modification of biomolecules. The synthetic capabilities of chiral [alpha][beta]-azidoisocyanides were systematically reviewed. The potential of using them as bifunctional building blocks for multicomponent Passerini and Ugi reactions and also for Cu(I)-catalyzed [3+2]-cycloaddition to form 1,2,3-triazoles was demonstrated. The bifunctional nature of these compounds enabled the development of a methodology for preparing peptides containing an azide group and conjugating them subsequently with various biologically active compounds containing an ethynyl group for targeted modification of biomolecules. Keywords: azidoisocyanides; peptides; Ugi reaction; Cu(I)-catalyzed [3+2]-cycloaddition; 1,2,3-triazoles; steroids; betulonic acid; betulinic acid; amino, hydroxy-, and phosphonic acids; phthalocyanine, methylphosphonates, carbolines. The synthetic capabilities of chiral [alpha][beta]-azidoisocyanides were systematically reviewed. The potential of using them as bifunctional building blocks for multicomponent Passerini and Ugi reactions and also for Cu(I)-catalyzed [3+2]-cycloaddition to form 1,2,3-triazoles was demonstrated. The bifunctional nature of these compounds enabled the development of a methodology for preparing peptides containing an azide group and conjugating them subsequently with various biologically active compounds containing an ethynyl group for targeted modification of biomolecules. |
| Audience | Academic |
| Author | Sokolova, N. V Nenajdenko, V. G |
| Author_xml | – sequence: 1 fullname: Sokolova, N. V – sequence: 2 fullname: Nenajdenko, V. G |
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| CitedBy_id | crossref_primary_10_1039_C9OB00229D crossref_primary_10_1021_acs_joc_3c00558 crossref_primary_10_1016_j_tet_2018_06_045 crossref_primary_10_1007_s10600_014_1167_6 crossref_primary_10_1002_ejoc_201900780 crossref_primary_10_1039_C6CS00444J crossref_primary_10_1002_chin_201431240 crossref_primary_10_1021_acs_chemrev_5b00302 |
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| Keywords | phthalocyanine, methylphosphonates, carbolines azidoisocyanides Ugi reaction peptides betulonic acid steroids amino, hydroxy-, and phosphonic acids Cu(I)-catalyzed [3+2]-cycloaddition betulinic acid 1,2,3-triazoles |
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| Snippet | The synthetic capabilities of chiral α,β-azidoisocyanides were systematically reviewed. The potential of using them as bifunctional building blocks for... The synthetic capabilities of chiral α , β -azidoisocyanides were systematically reviewed. The potential of using them as bifunctional building blocks for... The synthetic capabilities of chiral [alpha][beta]-azidoisocyanides were systematically reviewed. The potential of using them as bifunctional building blocks... |
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| SubjectTerms | azides Biochemistry chemical reactions Chemical tests and reagents copper cyanides Medicine molecular biology new methods Organic Chemistry Peptides Pharmacy Phthalocyanins Plant Sciences Triazoles |
| Title | Azidoisocyanides, New Bifunctional Reagents for Multicomponent Reactions and Biomolecule Modifications |
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