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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Bibliographic Details
Published inChemistry of natural compounds Vol. 50; no. 2; pp. 197 - 213
Main Authors Sokolova, N. V, Nenajdenko, V. G
Format Journal Article
LanguageEnglish
Published Boston Springer-Verlag 01.05.2014
Springer US
Springer
Subjects
azides
Biochemistry
chemical reactions
Chemical tests and reagents
copper
cyanides
Medicine
molecular biology
new methods
Organic Chemistry
Peptides
Pharmacy
Phthalocyanins
Plant Sciences
Triazoles
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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Summary: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.
Bibliography:http://dx.doi.org/10.1007/s10600-014-0914-z
ISSN:0009-3130
1573-8388
DOI:10.1007/s10600-014-0914-z