(R)-α-Trifluoromethylalanine as a 19F NMR Probe for the Monitoring of Protease Digestion of Peptides

被引:6
|
作者
Devillers, Emmanuelle [1 ,2 ]
Chelain, Evelyne [1 ,2 ]
Dalvit, Claudio [3 ,4 ]
Brigaud, Thierry [1 ,2 ]
Pytkowicz, Julien [1 ,2 ]
机构
[1] CY Cergy Paris Univ, CNRS, BIOCIS, 5 Mail Gay Lussac, F-95031 Neuville Sur Oise, Cergy Pontoise, France
[2] Univ Paris Saclay, BIOCIS, CNRS, F-92290 Chatenay Malabry, France
[3] Univ Neuchatel, Fac Sci, Ave Bellevaux 51, CH-2000 Neuchatel, Switzerland
[4] Lavis, Trento, Italy
关键词
FABS; NMR spectroscopy; pepsin; trifluoromethylated peptides; trypsin; PROTEOLYTIC STABILITY; PROLYL OLIGOPEPTIDASE; VERSATILE TOOL; LABEL; IDENTIFICATION; THERAPEUTICS; CHYMOTRYPSIN; FLUORINATION; EFFICIENT; DESIGN;
D O I
10.1002/cbic.202100470
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Fluorinated non-natural amino acids are useful tools for improving the bioavailability of peptides but can also serve as fluorinated probes in F-19 NMR-based enzymatic assays. We report herein that the use of the non-natural alpha-quaternarized (R)-alpha-trifluoromethylalanine ((R)-alpha-TfmAla) provides convenient and accurate monitoring of trypsin proteolytic activity and increases resistance towards pepsin degradation.
引用
下载
收藏
页数:5
相关论文
共 50 条
  • [21] 19F NMR OF SOME FLUOROQUINOLINES
    FRANZ, CA
    HALL, RT
    KASLOW, CE
    TETRAHEDRON LETTERS, 1967, (20) : 1947 - &
  • [22] Applications of 19F multidimensional NMR
    Battiste, J
    Newmark, RA
    PROGRESS IN NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY, 2006, 48 (01) : 1 - 23
  • [23] Synthesis of 4,6-Difluoro-Tryptophan as a Probe for Protein 19F NMR
    Monnie, Christina M.
    Hernandez, Iker
    Melendez-Pacheco, Raixie
    Bhinderwala, Fatema
    Soloshonok, Vadim A.
    Gronenborn, Angela M.
    Landa, Aitor
    Oiarbide, Mikel
    ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (16) : 3417 - 3422
  • [24] Synthesis of fluorinated maltose derivatives for monitoring protein interaction by 19F NMR
    Braitsch, Michaela
    Kaehlig, Hanspeter
    Kontaxis, Georg
    Fischer, Michael
    Kawada, Toshinari
    Konrat, Robert
    Schmid, Walther
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2012, 8 : 448 - 455
  • [25] Monitoring solid-phase glycoside synthesis with 19F NMR spectroscopy
    Mogemark, M
    Elofsson, M
    Kihlberg, J
    ORGANIC LETTERS, 2001, 3 (10) : 1463 - 1466
  • [26] Using O2 to probe membrane immersion depth by 19F NMR
    Prosser, RS
    Luchette, PA
    Westerman, PW
    PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2000, 97 (18) : 9967 - 9971
  • [27] 4,4-Difluoroproline as a Unique 19F NMR Probe of Proline Conformation
    Ganguly, Himal K.
    Ludwig, Brice A.
    Tressler, Caitlin M.
    Bhatt, Megh R.
    Pandey, Anil K.
    Quinn, Caitlin M.
    Bai, Shi
    Yap, Glenn P. A.
    Zondlo, Neal J.
    BIOCHEMISTRY, 2024, 63 (09) : 1131 - 1146
  • [28] Dual-Function Probe to Detect Protease Activity for Fluorescence Measurement and 19F MRI
    Mizukami, Shin
    Takikawa, Rika
    Sugihara, Fuminori
    Shirakawa, Masahiro
    Kikuchi, Kazuya
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (20) : 3641 - 3643
  • [29] 19F: A small probe for a giant protein
    Cosottini, Lucrezia
    Zineddu, Stefano
    Massai, Lara
    Ghini, Veronica
    Turano, Paola
    JOURNAL OF INORGANIC BIOCHEMISTRY, 2023, 244
  • [30] 2D 19F/19F NOESY for the assignment of NMR spectra of fluorochemicals
    Battiste, JL
    Jing, NY
    Newmark, PA
    JOURNAL OF FLUORINE CHEMISTRY, 2004, 125 (09) : 1331 - 1337