Monofluoroalkene-Isostere as a 19F NMR Label for the Peptide Backbone: Synthesis and Evaluation in Membrane-Bound PGLa and (KIGAKI)3

被引：17

作者：

Drouin, Myriam ^{[1
]}

Wadhwani, Parvesh ^{[2
]}

Grage, Stephan L. ^{[2
]}

Buerck, Jochen ^{[2
]}

Reichert, Johannes ^{[2
]}

Tremblay, Sebastien ^{[1
]}

Mayer, Marie Sabine ^{[1
,2
]}

Diel, Christian ^{[1
,2
]}

Staub, Alexander ^{[2
]}

Paquin, Jean-Francois ^{[1
]}

Ulrich, Anne S. ^{[2
]}

机构：

[1] Univ Laval, PROTEO, CCVC, Dept Chim, 1045 Ave Med, Quebec City, PQ G1V 0A6, Canada

[2] Karlsruhe Inst Technol, Inst Biol Interfaces IBG 2, POB 3640, D-76021 Karlsruhe, Germany

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2020年 / 26卷 / 07期

基金：

加拿大自然科学与工程研究理事会;

关键词：

F-19-labeled peptides; circular dichroism; monofluoroalkene; solid state F-19 NMR; vesicle leakage; PROTEIN SECONDARY STRUCTURE; CIRCULAR-DICHROISM SPECTRA; SOLID-STATE F-19-NMR; ANTIMICROBIAL PEPTIDE; AMINO-ACID; DIPEPTIDE; FLUORINE; DESIGN; AGGREGATION; ORIENTATION;

D O I：

10.1002/chem.201905054

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Solid-state F-19 NMR is a powerful method to study the interactions of biologically active peptides with membranes. So far, in labelled peptides, the F-19-reporter group has always been installed on the side chain of an amino acid. Given the fact that monofluoroalkenes are non-hydrolyzable peptide bond mimics, we have synthesized a monofluoroalkene-based dipeptide isostere, Val-psi[(Z)-CF=CH]-Gly, and inserted it in the sequence of two well-studied antimicrobial peptides: PGLa and (KIGAKI)(3) are representatives of an alpha-helix and a beta-sheet. The conformations and biological activities of these labeled peptides were studied to assess the suitability of monofluoroalkenes for F-19 NMR structure analysis.

引用

页码：1511 / 1517

页数：7

共 70 条

[1] 4-Fluorophenylglycine as a label for 19F NMR structure analysis of membrane-associated peptides [J].