17α-Ethynylestradiol Peptide Labeling by ‘Click’ Chemistry

Oleg I. Bol’shakov; Iryna O. Lebedyeva; Alan R. Katritzky

doi:10.1055/s-0032-1316702

Synthesis, Inhaltsverzeichnis

Synthesis 2012; 44(18): 2926-2932
DOI: 10.1055/s-0032-1316702

paper

17α-Ethynylestradiol Peptide Labeling by ‘Click’ Chemistry

Oleg I. Bol’shakov

^aCenter for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA, Fax: +1(352)3929199 eMail: katritzky@chem.ufl.edu

,

Iryna O. Lebedyeva

^aCenter for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA, Fax: +1(352)3929199 eMail: katritzky@chem.ufl.edu

,

Alan R. Katritzky*

^aCenter for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA, Fax: +1(352)3929199 eMail: katritzky@chem.ufl.edu

^bChemistry Department, King Abdulaziz University, Jeddah, 21589, Saudi Arabia

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Abstract

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Abstract

A synthesis of 17α-ethynylestradiol-labeled native peptides is reported. The peptide moiety is tethered to the steroid hormone by a 1,2,3-triazole bridge formed by a CuAAC reaction in which the azido group of the peptide combines with the terminal acetylenic moiety of ethynylestradiol to link the two bioactive molecules. Thus bioconjugates containing the hormone moiety at three positions within the peptide molecule could be useful targets for hormono–enzyme interaction studies.

Key words

cyclization - azides - alkynes - peptides - drugs - click chemistry

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