Metal-mediated formation of gas-phase amino acid radical cations

Christopher K. Barlow; Damian Moran; Leo Radom; W. David McFadyen; Richard A.J. O'Hair

doi:10.1021/jp056471v

Metal-mediated formation of gas-phase amino acid radical cations

Christopher K. Barlow, Damian Moran, Leo Radom, W. David McFadyen, Richard A.J. O'Hair

Research output: Contribution to journal › Article › Research › peer-review

62 Citations (Scopus)

Abstract

The results from an investigation of the collision-induced dissociation (CID) of the ternary complexes [Cu ^II(terpy)(AA)] ²⁺ are presented (terpy = 2,2′:6′,2″-terpyridine; AA = one of the twenty common amino acids). These complexes show a rich gas-phase chemistry, which depends on the identity of the amino acid. For the histidine-, lysine- and tryptophan-containing complexes, oxidative dissociation of the amino acid is observed, yielding the amino acid radical cation. The results of further mass selection and CID of these amino acid radical cations are presented. The CID of the series [Fe ^III(salen)(AA)] ⁺ (where salen = N,N′-ethylenebis(salicylideneaminato)) is also examined. These complexes undergo loss of the neutral amino acid in all cases, although the radical cation of arginine is also produced and its subsequent fragmentation examined. B3-LYP/6-31_G(d) computations were carried out to test aspects of the proposed fragmentation mechanism of the histidine and arginine radical cations.

Original language	English
Pages (from-to)	8304-8315
Number of pages	12
Journal	The Journal of Physical Chemistry A
Volume	110
Issue number	27
DOIs	https://doi.org/10.1021/jp056471v
Publication status	Published - 13 Jul 2006
Externally published	Yes

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10.1021/jp056471v

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title = "Metal-mediated formation of gas-phase amino acid radical cations",

abstract = "The results from an investigation of the collision-induced dissociation (CID) of the ternary complexes [Cu II(terpy)(AA)] 2+ are presented (terpy = 2,2′:6′,2″-terpyridine; AA = one of the twenty common amino acids). These complexes show a rich gas-phase chemistry, which depends on the identity of the amino acid. For the histidine-, lysine- and tryptophan-containing complexes, oxidative dissociation of the amino acid is observed, yielding the amino acid radical cation. The results of further mass selection and CID of these amino acid radical cations are presented. The CID of the series [Fe III(salen)(AA)] + (where salen = N,N′-ethylenebis(salicylideneaminato)) is also examined. These complexes undergo loss of the neutral amino acid in all cases, although the radical cation of arginine is also produced and its subsequent fragmentation examined. B3-LYP/6-31\_G(d) computations were carried out to test aspects of the proposed fragmentation mechanism of the histidine and arginine radical cations.",

author = "Barlow, \{Christopher K.\} and Damian Moran and Leo Radom and McFadyen, \{W. David\} and O'Hair, \{Richard A.J.\}",

year = "2006",

month = jul,

day = "13",

doi = "10.1021/jp056471v",

language = "English",

volume = "110",

pages = "8304--8315",

journal = "The Journal of Physical Chemistry A",

issn = "1089-5639",

publisher = "American Chemical Society",

number = "27",

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TY - JOUR

T1 - Metal-mediated formation of gas-phase amino acid radical cations

AU - Barlow, Christopher K.

AU - Moran, Damian

AU - Radom, Leo

AU - McFadyen, W. David

AU - O'Hair, Richard A.J.

PY - 2006/7/13

Y1 - 2006/7/13

N2 - The results from an investigation of the collision-induced dissociation (CID) of the ternary complexes [Cu II(terpy)(AA)] 2+ are presented (terpy = 2,2′:6′,2″-terpyridine; AA = one of the twenty common amino acids). These complexes show a rich gas-phase chemistry, which depends on the identity of the amino acid. For the histidine-, lysine- and tryptophan-containing complexes, oxidative dissociation of the amino acid is observed, yielding the amino acid radical cation. The results of further mass selection and CID of these amino acid radical cations are presented. The CID of the series [Fe III(salen)(AA)] + (where salen = N,N′-ethylenebis(salicylideneaminato)) is also examined. These complexes undergo loss of the neutral amino acid in all cases, although the radical cation of arginine is also produced and its subsequent fragmentation examined. B3-LYP/6-31_G(d) computations were carried out to test aspects of the proposed fragmentation mechanism of the histidine and arginine radical cations.

AB - The results from an investigation of the collision-induced dissociation (CID) of the ternary complexes [Cu II(terpy)(AA)] 2+ are presented (terpy = 2,2′:6′,2″-terpyridine; AA = one of the twenty common amino acids). These complexes show a rich gas-phase chemistry, which depends on the identity of the amino acid. For the histidine-, lysine- and tryptophan-containing complexes, oxidative dissociation of the amino acid is observed, yielding the amino acid radical cation. The results of further mass selection and CID of these amino acid radical cations are presented. The CID of the series [Fe III(salen)(AA)] + (where salen = N,N′-ethylenebis(salicylideneaminato)) is also examined. These complexes undergo loss of the neutral amino acid in all cases, although the radical cation of arginine is also produced and its subsequent fragmentation examined. B3-LYP/6-31_G(d) computations were carried out to test aspects of the proposed fragmentation mechanism of the histidine and arginine radical cations.

UR - https://www.scopus.com/pages/publications/33746418924

U2 - 10.1021/jp056471v

DO - 10.1021/jp056471v

M3 - Article

C2 - 16821814

AN - SCOPUS:33746418924

SN - 1089-5639

VL - 110

SP - 8304

EP - 8315

JO - The Journal of Physical Chemistry A

JF - The Journal of Physical Chemistry A

IS - 27

ER -

Metal-mediated formation of gas-phase amino acid radical cations

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ARC Centre of Excellence - Centre for Free Radical Chemistry and Biotechnology

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Metal-mediated formation of gas-phase amino acid radical cations

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ARC Centre of Excellence - Centre for Free Radical Chemistry and Biotechnology

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