Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Backbone-Fluorinated 1,2,3-Triazole-Containing Dipeptide Surrogates

Backbone-Fluorinated 1,2,3-Triazole-Containing Dipeptide Surrogates
Jens Engel-Andreasen, Christian A. Olsen, Kathrine Wich, Isabelle Wellhöfer
The 1,2,3-triazole moiety can be incorporated as a peptide bond bioisostere to provide protease resistance in peptidomimetics. Herein, we report the synthesis of peptidomimetic building blocks containing backbone-fluorinated 1,4-disubstituted 1,2,3-triazole moieties. Synthetic protocols for the preparation of various Xaa-Gly dipeptide surrogates in the form of Xaa-ψ[triazole]-F2Gly building blocks were established, and selected examples were introduced into the endogenous peptide opioid receptor ligand Leu-enkephalin as a model compound.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01744

DOI: 10.1021/acs.joc.7b01744

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