TY - JOUR
T1 - Backbone-Fluorinated 1,2,3-Triazole-Containing Dipeptide Surrogates
AU - Engel-Andreasen, Jens
AU - Wellhöfer, Isabelle
AU - Wich, Kathrine
AU - Olsen, Christian A
PY - 2017/11/3
Y1 - 2017/11/3
N2 - 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.
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
U2 - 10.1021/acs.joc.7b01744
DO - 10.1021/acs.joc.7b01744
M3 - Journal article
C2 - 28985056
SN - 0022-3263
VL - 82
SP - 11613
EP - 11619
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 21
ER -