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

被引:80
作者
Cheng, Ming [1 ]
Zhang, Bojie [1 ]
Cui, Weidong [1 ]
Gross, Michael L. [1 ]
机构
[1] Washington Univ, Dept Chem, One Brookings Dr, St Louis, MO 63130 USA
基金
美国国家卫生研究院;
关键词
amino acids; mass spectrometry; membrane proteins; radical reactions; reaction mechanisms; DE-NOVO SYNTHESIS; CAPSULAR POLYSACCHARIDE VACCINE; PNEUMONIAE SEROTYPE 4; KLEBSIELLA-PNEUMONIAE; CONJUGATE VACCINES; REPEATING UNIT; SYNTHETIC OLIGOSACCHARIDES; CHEMICAL-SYNTHESIS; URONIC-ACIDS; SIALIC-ACID;
D O I
10.1002/anie.201706697
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Described is a novel, laser-initiated radical trifluoromethylation for protein footprinting and its broad residue coverage. center dot 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 COH. This new approach to footprinting is a bridge between trifluoromethylation in materials and medicinal chemistry and structural biology and biotechnology. Its application toamembrane protein and to myoglobin show that the approach is sensitive to protein conformational change and solvent accessibility.
引用
收藏
页码:14007 / 14010
页数:4
相关论文
共 76 条
  • [1] Synthetically defined glycoprotein vaccines: current status and future directions
    Adamo, Roberto
    Nilo, Alberto
    Castagner, Bastien
    Boutureira, Omar
    Berti, Francesco
    Bernardes, Gonalo J. L.
    [J]. CHEMICAL SCIENCE, 2013, 4 (08) : 2995 - 3008
  • [2] Development of immunization trials against Klebsiella pneumoniae
    Ahmad, Tarek A.
    El-Sayed, Laila H.
    Haroun, Medhat
    Hussein, Ahmad A.
    El Ashry, El Sayed H.
    [J]. VACCINE, 2012, 30 (14) : 2411 - 2420
  • [3] [Anonymous], 2011, ANGEW CHEM
  • [4] Carbohydrate vaccines: developing sweet solutions to sticky situations?
    Astronomo, Rena D.
    Burton, Dennis R.
    [J]. NATURE REVIEWS DRUG DISCOVERY, 2010, 9 (04) : 308 - 324
  • [5] De novo synthesis of oligosaccharides using a palladium-catalyzed glycosylation reaction
    Babu, RS
    Zhou, M
    O'Doherty, GA
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (11) : 3428 - 3429
  • [6] Total Synthesis of the Phenolic Glycolipid Mycoside B and the Glycosylated p-Hydroxybenzoic Acid Methyl Ester HBAD-I, Virulence Markers of Mycobacterium tuberculosis
    Barroso, Santiago
    Geerdink, Danny
    ter Horst, Bjorn
    Casas-Arce, Eva
    Minnaard, Adriaan J.
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (21) : 4642 - 4654
  • [7] ISOMERIZATION OF ALLYL ETHERS CATALYZED BY CATIONIC IRIDIUM COMPLEX [IR(CYCLO-OCTA-1,5-DIENE)(PMEPH2)2]PF6 - HIGHLY STEREOSELECTIVE ROUTE TO TRANS-PROPENYL ETHERS
    BAUDRY, D
    EPHRITIKHINE, M
    FELKIN, H
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (16) : 694 - 695
  • [8] Outcome of carbapenem resistant Klebsiella pneumoniae bloodstream infections
    Ben-David, D.
    Kordevani, R.
    Keller, N.
    Tal, I.
    Marzel, A.
    Gal-Mor, O.
    Maor, Y.
    Rahav, G.
    [J]. CLINICAL MICROBIOLOGY AND INFECTION, 2012, 18 (01) : 54 - 60
  • [9] STUDY OF C-13H COUPLING-CONSTANTS IN HEXOPYRANOSES
    BOCK, K
    PEDERSEN, C
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1974, (03): : 293 - 299
  • [10] Boltje TJ, 2009, NAT CHEM, V1, P611, DOI [10.1038/NCHEM.399, 10.1038/nchem.399]