Conformationally rigid trifluoromethyl-substituted α-amino acid designed for peptide structure analysis by solid-state 19F NMR spectroscopy

被引：95

作者：

Mikhailiuk, Pavel K.

Afonin, Sergii

Chernega, Alerander N.

Rusanov, Eduard B.

Platonov, Maxini O.

Dubinina, Galina G.

Berditsch, Marina

UIrich, Anne S.

Komarov, Igor V.

机构：

[1] Univ Karlsruhe, Inst Organ Chem, D-76133 Karlsruhe, Germany

[2] Kyiv Natl Taras Shvchenko Univ, Dept Chem, UA-01033 Kiev, Ukraine

[3] Enamine Ltd, UA-01103 Kiev, Ukraine

[4] NAS Ukraine, Inst Organ Chem, UA-02094 Kiev, Ukraine

[5] Inst Biol Grenzflachen, Forschungszentrum Karlsruhe, D-76344 Eggenstein Leopoldshafen, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2006年 / 45卷 / 34期

关键词：

amino acids; fluorine; membrane-active peptides; NMR spectroscopy;

D O I：

10.1002/anie.200600346

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Figure Presented) Designing a sturdy label: The fluorinated amino acid L-CF3-Bpg (see picture), which was specifically designed as a 19F NMR label for structure analysis of membrane-bound peptides, does not display the drawbacks of previously used labels. The amino acid can be readily incorporated into peptides and is particularly suitable as a substitute for Leu, Ile, and Met. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：5659 / 5661

页数：3

共 50 条

[1] Synthesis of trifluoromethyl-substituted proline analogues as 19F NMR labels for peptides in the polyproline II conformation
Mykhailiuk, Pavel K.
Afonin, Sergii
Palamarchuk, Gennady V.
Shishkin, Oleg V.
Ulrich, Anne S.
Komarov, Igor V.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (31) : 5765 - 5767
[2] Solid-State Organization of Semifluorinated Alkanes Probed by 19F MAS NMR Spectroscopy
Lee, Young Joo
Clark, Christopher G., Jr.
Graf, Robert
Wagner, Manfred
Muellen, Klaus
Spiess, Hans Wolfgang
JOURNAL OF PHYSICAL CHEMISTRY B, 2009, 113 (05): : 1360 - 1366
[3] Metrologically traceable quantification of trifluoroacetic acid content in peptide reference materials by 19F solid-state NMR
Brinkmann, Andreas
Raza, Mohammad
Melanson, Jeremy E.
METROLOGIA, 2019, 56 (02)
[4] 19F Solid-state NMR characterization of pharmaceutical solids*
Du, Yong
Su, Yongchao
SOLID STATE NUCLEAR MAGNETIC RESONANCE, 2022, 120
[5] Design, Synthesis, and Application of an Optimized Monofluorinated Aliphatic Label for Peptide Studies by Solid-State 19F NMR Spectroscopy
Kokhan, Serhii O.
Tymtsunik, Andriy V.
Grage, Stephan L.
Afonin, Sergii
Babii, Oleg
Berditsch, Marina
Strizhak, Alexander V.
Bandak, Dmytro
Platonov, Maxim O.
Komarov, Igor V.
Ulrich, Anne S.
Mykhailiuk, Pavel K.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (47) : 14788 - 14792
[6] Semicrystallinity and polymorphism in PVDF:: a solid-state 19F nmr investigation
Holstein, P
Scheler, U
Harris, RK
POLYMER, 1998, 39 (20) : 4937 - 4941
[7] Peptide structural analysis by solid-state NMR spectroscopy
Bechinger, B
Kinder, R
Helmle, M
Vogt, TCB
Harzer, U
Schinzel, S
BIOPOLYMERS, 1999, 51 (03) : 174 - 190
[8] Structure and dynamics of perfluoroalkane/β-cyclodextrin inclusion compounds as studied by solid-state 19F MAS and 1H →19F CP/MAS NMR spectroscopy
Tatsuno, Hiroto
Ando, Shinji
JOURNAL OF PHYSICAL CHEMISTRY B, 2006, 110 (51): : 25751 - 25760
[9] 19F solid-state NMR approaches to probe antimicrobial peptide interactions with membranes in whole cells
Kumar, Kiran
Arnold, Alexandre A.
Gauthier, Raphael
Mamone, Marius
Paquin, Jean-Francois
Warschawski, Dror E.
Marcotte, Isabelle
BIOCHIMICA ET BIOPHYSICA ACTA-BIOMEMBRANES, 2024, 1866 (03):
[10] Simultaneous assessment of membrane bilayer structure and drug insertion by 19F solid-state NMR
Kumar, Kiran
Arnold, Alexandre A.
Gauthier, Raphael
Mamone, Marius
Paquin, Jean-Francois
Warschawski, Dror E.
Marcotte, Isabelle
BIOPHYSICAL JOURNAL, 2025, 124 (02) : 256 - 266

← 1 2 3 4 5 →