Design and synthesis of bile acid–peptide conjugates linked via triazole moiety

Nadezhda V. Sokolova; Gennadij V. Latyshev; Nikolay V. Lukashev; Valentine G. Nenajdenko

doi:10.1039/C0OB01188F

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Organic & Biomolecular Chemistry

Issue 13, 2011

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Design and synthesis of bile acid–peptide conjugates linked via triazole moiety

Nadezhda V. Sokolova , Gennadij V. Latyshev , Nikolay V. Lukashev and Valentine G. Nenajdenko

Org. Biomol. Chem., 2011,9, 4921-4926

DOI: 10.1039/C0OB01188F
Received 16 Dec 2010, Accepted 11 Apr 2011
First published on the web 12 Apr 2011

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A conjugation of bile acids with peptides via Cu(I)-catalyzed click chemistry has been described. Novel bile acid–peptide conjugates linked via a 1,2,3-triazole moiety based on cholic, deoxycholic and lithocholic acid derivatives were synthesized using Cu(I)-catalyzed 1,3-dipolar cycloaddition (“click” reaction). It was shown that up to three peptide fragments can be attached to a central steroid core, thus forming complex three-dimensional polyconjugate structures, which can find important applications in biochemistry, medicinal chemistry, and coordination chemistry.