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Title: Photodissociative Cross-Linking of Non-covalent Peptide-Peptide Ion Complexes in the Gas Phase

Abstract

We report a gas-phase UV photodissociation study investigating non-covalent interactions between neutral hydrophobic pentapeptides and peptide ions incorporating a diazirine-tagged photoleucine residue. Phenylalanine (Phe) and proline (Pro) were chosen as the conformation-affecting residues that were incorporated into a small library of neutral pentapeptides. Gas-phase ion-molecule complexes of these peptides with photo-labeled pentapeptides were subjected to photodissociation. Selective photocleavage of the diazirine ring at 355 nm formed short-lived carbene intermediates that underwent cross-linking by insertion into H–X bonds of the target peptide. The cross-link positions were established from collision-induced dissociation tandem mass spectra (CID-MS{sup 3}) providing sequence information on the covalent adducts. Effects of the amino acid residue (Pro or Phe) and its position in the target peptide sequence were evaluated. For proline-containing peptides, interactions resulting in covalent cross-links in these complexes became more prominent as proline was moved towards the C-terminus of the target peptide sequence. The photocross-linking yields of phenylalanine-containing peptides depended on the position of both phenylalanine and photoleucine. Density functional theory calculations were used to assign structures of low-energy conformers of the (GLPMG + GLL*LK + H){sup +} complex. Born-Oppenheimer molecular dynamics trajectory calculations were used to capture the thermal motion in the complexes within 100 ps and determinemore » close contacts between the incipient carbene and the H–X bonds in the target peptide. This provided atomic-level resolution of potential cross-links that aided spectra interpretation and was in agreement with experimental data. .« less

Authors:
 [1];  [2];  [3];  [4];  [1]
  1. University of Washington, Department of Chemistry, Bagley Hall (United States)
  2. Czech Academy of Sciences, Laboratory of Biomolecular Recognition, Institute of Biotechnology (Czech Republic)
  3. Czech Academy of Sciences, Institute of Organic Chemistry and Biochemistry (Czech Republic)
  4. Valspar Corporation (United States)
Publication Date:
OSTI Identifier:
22776869
Resource Type:
Journal Article
Journal Name:
Journal of the American Society for Mass Spectrometry
Additional Journal Information:
Journal Volume: 29; Journal Issue: 8; Other Information: Copyright (c) 2018 American Society for Mass Spectrometry; http://www.springer-ny.com; Country of input: International Atomic Energy Agency (IAEA); Journal ID: ISSN 1044-0305
Country of Publication:
United States
Language:
English
Subject:
74 ATOMIC AND MOLECULAR PHYSICS; BORN-OPPENHEIMER APPROXIMATION; CAPTURE; COLLISIONS; DENSITY FUNCTIONAL METHOD; DISSOCIATION; INTERACTIONS; MASS SPECTRA; MOLECULAR DYNAMICS METHOD; PEPTIDES; PHENYLALANINE; PROLINE

Citation Formats

Nguyen, Huong T. H., Andrikopoulos, Prokopis C., Rulíšek, Lubomír, Shaffer, Christopher J., and Tureček, František. Photodissociative Cross-Linking of Non-covalent Peptide-Peptide Ion Complexes in the Gas Phase. United States: N. p., 2018. Web. doi:10.1007/S13361-018-1980-4.
Nguyen, Huong T. H., Andrikopoulos, Prokopis C., Rulíšek, Lubomír, Shaffer, Christopher J., & Tureček, František. Photodissociative Cross-Linking of Non-covalent Peptide-Peptide Ion Complexes in the Gas Phase. United States. doi:10.1007/S13361-018-1980-4.
Nguyen, Huong T. H., Andrikopoulos, Prokopis C., Rulíšek, Lubomír, Shaffer, Christopher J., and Tureček, František. Wed . "Photodissociative Cross-Linking of Non-covalent Peptide-Peptide Ion Complexes in the Gas Phase". United States. doi:10.1007/S13361-018-1980-4.
@article{osti_22776869,
title = {Photodissociative Cross-Linking of Non-covalent Peptide-Peptide Ion Complexes in the Gas Phase},
author = {Nguyen, Huong T. H. and Andrikopoulos, Prokopis C. and Rulíšek, Lubomír and Shaffer, Christopher J. and Tureček, František},
abstractNote = {We report a gas-phase UV photodissociation study investigating non-covalent interactions between neutral hydrophobic pentapeptides and peptide ions incorporating a diazirine-tagged photoleucine residue. Phenylalanine (Phe) and proline (Pro) were chosen as the conformation-affecting residues that were incorporated into a small library of neutral pentapeptides. Gas-phase ion-molecule complexes of these peptides with photo-labeled pentapeptides were subjected to photodissociation. Selective photocleavage of the diazirine ring at 355 nm formed short-lived carbene intermediates that underwent cross-linking by insertion into H–X bonds of the target peptide. The cross-link positions were established from collision-induced dissociation tandem mass spectra (CID-MS{sup 3}) providing sequence information on the covalent adducts. Effects of the amino acid residue (Pro or Phe) and its position in the target peptide sequence were evaluated. For proline-containing peptides, interactions resulting in covalent cross-links in these complexes became more prominent as proline was moved towards the C-terminus of the target peptide sequence. The photocross-linking yields of phenylalanine-containing peptides depended on the position of both phenylalanine and photoleucine. Density functional theory calculations were used to assign structures of low-energy conformers of the (GLPMG + GLL*LK + H){sup +} complex. Born-Oppenheimer molecular dynamics trajectory calculations were used to capture the thermal motion in the complexes within 100 ps and determine close contacts between the incipient carbene and the H–X bonds in the target peptide. This provided atomic-level resolution of potential cross-links that aided spectra interpretation and was in agreement with experimental data. .},
doi = {10.1007/S13361-018-1980-4},
journal = {Journal of the American Society for Mass Spectrometry},
issn = {1044-0305},
number = 8,
volume = 29,
place = {United States},
year = {2018},
month = {8}
}