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

Jens Engel-Andreasen; Isabelle Wellhöfer; Kathrine Wich; Christian A Olsen

doi:10.1021/acs.joc.7b01744

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

Jens Engel-Andreasen, Isabelle Wellhöfer, Kathrine Wich, Christian A Olsen

4 Citations (Scopus)

Abstract

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.

Original language	English
Journal	Journal of Organic Chemistry
Volume	82
Issue number	21
Pages (from-to)	11613-11619
ISSN	0022-3263
DOIs	https://doi.org/10.1021/acs.joc.7b01744
Publication status	Published - 3 Nov 2017

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10.1021/acs.joc.7b01744

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abstract = "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.",

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AU - Engel-Andreasen, Jens

AU - Wellhöfer, Isabelle

AU - Wich, Kathrine

AU - Olsen, Christian A

PY - 2017/11/3

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AB - 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.

KW - Journal Article

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JF - Journal of Organic Chemistry

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ER -

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

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