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

被引：13

作者：

Engel-Andreasen, Jens ^{[2
]}

Wellhofer, Isabelle

Wich, Kathrine ^{[3
]}

Olsen, Christian A. ^{[1
]}

机构：

[1] Univ Copenhagen, Ctr Biopharmaceut, Fac Hlth & Med Sci, Univ Pk 2, DK-2100 Copenhagen, Denmark

[2] Chr Hansen AS, Horsholm, Denmark

[3] QIAGEN GmbH, Hilden, Germany

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 21期

关键词：

AMINO-ACIDS; SOLID-PHASE; CLICK CHEMISTRY; PEPTIDE; FOLDAMERS; TRIAZOLE; MIMICS; BOND; ALKYNES; DESIGN;

D O I：

10.1021/acs.joc.7b01744

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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-Psi[triazol]-F(2)Gly building blocks were established, and selected examples were introduced into the endogenous peptide opioid receptor ligand Leu-enkephalin Leu-enkephalin as a model compound.

引用

页码：11613 / 11619

页数：7

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