Monofluoroalkene-Isostere as a 19 Fâ
NMR Label for the Peptide Backbone: Synthesis and Evaluation in Membrane-Bound PGLa and (KIGAKI)3.
Chemistry
; 26(7): 1511-1517, 2020 Feb 03.
Article
em En
| MEDLINE
| ID: mdl-31867761
ABSTRACT
Solid-state 19 Fâ
NMR is a powerful method to study the interactions of biologically active peptides with membranes. So far, in labelled peptides, the 19 F-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-Ψ[(Z)-CF=CH]-Gly, and inserted it in the sequence of two well-studied antimicrobial peptides PGLa and (KIGAKI)3 are representatives of an α-helix and a ß-sheet. The conformations and biological activities of these labeled peptides were studied to assess the suitability of monofluoroalkenes for 19 Fâ
NMR structure analysis.
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MEDLINE
Assunto principal:
Espectroscopia de Ressonância Magnética
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Membrana Celular
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Peptídeos Catiônicos Antimicrobianos
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Idioma:
En
Ano de publicação:
2020
Tipo de documento:
Article