Literature DB >> 28901679

Laser-Initiated Radical Trifluoromethylation of Peptides and Proteins: Application to Mass-Spectrometry-Based Protein Footprinting.

Ming Cheng1, Bojie Zhang1, Weidong Cui1, Michael L Gross1.   

Abstract

Described is a novel, laser-initiated radical trifluoromethylation for protein footprinting and its broad residue coverage. . CF3 reacts with 18 of the 20 common amino acids, including Gly, Ala, Ser, Thr, Asp, and Glu, which are relatively silent with regard to . OH. This new approach to footprinting is a bridge between trifluoromethylation in materials and medicinal chemistry and structural biology and biotechnology. Its application to a membrane protein and to myoglobin show that the approach is sensitive to protein conformational change and solvent accessibility.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  amino acids; mass spectrometry; membrane proteins; radical reactions; reaction mechanisms

Mesh:

Substances:

Year:  2017        PMID: 28901679      PMCID: PMC5663992          DOI: 10.1002/anie.201706697

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  41 in total

Review 1.  Catalysis for fluorination and trifluoromethylation.

Authors:  Takeru Furuya; Adam S Kamlet; Tobias Ritter
Journal:  Nature       Date:  2011-05-26       Impact factor: 49.962

2.  Antigen-antibody interface properties: composition, residue interactions, and features of 53 non-redundant structures.

Authors:  Thiruvarangan Ramaraj; Thomas Angel; Edward A Dratz; Algirdas J Jesaitis; Brendan Mumey
Journal:  Biochim Biophys Acta       Date:  2012-01-10

3.  A method for probing the topography and interactions of proteins: footprinting of myoglobin.

Authors:  M Zhong; L Lin; N R Kallenbach
Journal:  Proc Natl Acad Sci U S A       Date:  1995-03-14       Impact factor: 11.205

4.  Trifluoromethylation of arenes and heteroarenes by means of photoredox catalysis.

Authors:  David A Nagib; David W C MacMillan
Journal:  Nature       Date:  2011-12-08       Impact factor: 49.962

5.  High-resolution mapping of carbene-based protein footprints.

Authors:  Chanelle C Jumper; Ryan Bomgarden; John Rogers; Chris Etienne; David C Schriemer
Journal:  Anal Chem       Date:  2012-04-25       Impact factor: 6.986

6.  Benzylic C(sp(3) )H Perfluoroalkylation of Six-Membered Heteroaromatic Compounds.

Authors:  Yoichiro Kuninobu; Masahiro Nagase; Motomu Kanai
Journal:  Angew Chem Int Ed Engl       Date:  2015-07-29       Impact factor: 15.336

7.  Practical method for the Cu-mediated trifluoromethylation of arylboronic acids with CF3 radicals derived from NaSO2CF3 and tert-butyl hydroperoxide (TBHP).

Authors:  Yingda Ye; Stefan A Künzi; Melanie S Sanford
Journal:  Org Lett       Date:  2012-09-17       Impact factor: 6.005

8.  Protein Footprinting by Carbenes on a Fast Photochemical Oxidation of Proteins (FPOP) Platform.

Authors:  Bojie Zhang; Don L Rempel; Michael L Gross
Journal:  J Am Soc Mass Spectrom       Date:  2015-12-17       Impact factor: 3.109

9.  Solvent mimicry with methylene carbene to probe protein topography.

Authors:  Gabriela Elena Gómez; José Luis E Monti; Mariana Rocío Mundo; José María Delfino
Journal:  Anal Chem       Date:  2015-09-30       Impact factor: 6.986

10.  Carbene footprinting accurately maps binding sites in protein-ligand and protein-protein interactions.

Authors:  Lucio Manzi; Andrew S Barrow; Daniel Scott; Robert Layfield; Timothy G Wright; John E Moses; Neil J Oldham
Journal:  Nat Commun       Date:  2016-11-16       Impact factor: 14.919

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  30 in total

1.  A Single Approach Reveals the Composite Conformational Changes, Order of Binding, and Affinities for Calcium Binding to Calmodulin.

Authors:  Xiaoran Roger Liu; Mengru Mira Zhang; Don L Rempel; Michael L Gross
Journal:  Anal Chem       Date:  2019-04-10       Impact factor: 6.986

2.  A Fast Photochemical Oxidation of Proteins (FPOP) platform for free-radical reactions: the carbonate radical anion with peptides and proteins.

Authors:  Mengru Mira Zhang; Don L Rempel; Michael L Gross
Journal:  Free Radic Biol Med       Date:  2018-11-28       Impact factor: 7.376

Review 3.  Fast photochemical oxidation of proteins (FPOP): A powerful mass spectrometry-based structural proteomics tool.

Authors:  Danté T Johnson; Luciano H Di Stefano; Lisa M Jones
Journal:  J Biol Chem       Date:  2019-07-01       Impact factor: 5.157

4.  Composite Conformational Changes of Signaling Proteins upon Ligand Binding Revealed by a Single Approach: Calcium-Calmodulin Study.

Authors:  Xiaoran Roger Liu; Don L Rempel; Michael L Gross
Journal:  Anal Chem       Date:  2019-09-12       Impact factor: 6.986

Review 5.  Covalent labeling-mass spectrometry with non-specific reagents for studying protein structure and interactions.

Authors:  Patanachai Limpikirati; Tianying Liu; Richard W Vachet
Journal:  Methods       Date:  2018-04-07       Impact factor: 3.608

6.  Protein-Metal-Ion Interactions Studied by Mass Spectrometry-Based Footprinting with Isotope-Encoded Benzhydrazide.

Authors:  Chunyang Guo; Ming Cheng; Michael L Gross
Journal:  Anal Chem       Date:  2018-12-12       Impact factor: 6.986

7.  Fast Protein Footprinting by X-ray Mediated Radical Trifluoromethylation.

Authors:  Ming Cheng; Awuri Asuru; Janna Kiselar; George Mathai; Mark R Chance; Michael L Gross
Journal:  J Am Soc Mass Spectrom       Date:  2020-04-21       Impact factor: 3.109

8.  Covalent Labeling with an α,β-Unsaturated Carbonyl Scaffold for Studying Protein Structure and Interactions by Mass Spectrometry.

Authors:  Bo Zhao; Jiaming Zhuang; Miaowei Xu; Tianying Liu; Patanachai Limpikirati; S Thayumanavan; Richard W Vachet
Journal:  Anal Chem       Date:  2020-04-14       Impact factor: 6.986

Review 9.  Implementing fast photochemical oxidation of proteins (FPOP) as a footprinting approach to solve diverse problems in structural biology.

Authors:  Bojie Zhang; Ming Cheng; Don Rempel; Michael L Gross
Journal:  Methods       Date:  2018-05-23       Impact factor: 3.608

Review 10.  Mass spectrometry-based methods in characterization of the higher order structure of protein therapeutics.

Authors:  Igor A Kaltashov; Cedric E Bobst; Jake Pawlowski; Guanbo Wang
Journal:  J Pharm Biomed Anal       Date:  2020-02-12       Impact factor: 3.935

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