Transnitrosylation products of the dipeptide cysteinyl-cysteine: An examination by tandem mass spectrometry and density functional theory
The fragmentation pathways of protonated mono-and di-nitrosylated derivatives from the dipeptide Cys-Cys obtained by electrospray were examined. Protonated mononitrosylated dipeptide upon loss of NO formed a radical cation, which in turn shows two fragment ions, one from the loss of HS and the other...
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Royal Society of Chemistry
2016
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| Acceso en línea: | Registro en Scopus DOI Handle Registro en la Biblioteca Digital |
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| LEADER | 06750caa a22008177a 4500 | ||
|---|---|---|---|
| 001 | PAPER-16363 | ||
| 003 | AR-BaUEN | ||
| 005 | 20230518204722.0 | ||
| 008 | 190411s2016 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-84958972650 | |
| 024 | 7 | |2 cas |a cysteine, 4371-52-2, 52-89-1, 52-90-4; Cysteine; cysteinylcysteine; Dipeptides | |
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 030 | |a PPCPF | ||
| 100 | 1 | |a Butler, M. | |
| 245 | 1 | 0 | |a Transnitrosylation products of the dipeptide cysteinyl-cysteine: An examination by tandem mass spectrometry and density functional theory |
| 260 | |b Royal Society of Chemistry |c 2016 | ||
| 270 | 1 | 0 | |m Butler, M.; Department of Chemistry and Centre for Research in Mass Spectrometry, York University, 4700 Keele Street, Canada; email: mbutler@qo.fcen.uba.ar |
| 506 | |2 openaire |e Política editorial | ||
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| 504 | |a Lam, A.K.Y., Ryzhov, V., O'Hair, R.A.J., (2010) J. Am. Soc. Mass Spectrom., 21, p. 1296 | ||
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| 520 | 3 | |a The fragmentation pathways of protonated mono-and di-nitrosylated derivatives from the dipeptide Cys-Cys obtained by electrospray were examined. Protonated mononitrosylated dipeptide upon loss of NO formed a radical cation, which in turn shows two fragment ions, one from the loss of HS and the other from a neutral loss giving a radical cation of formula C2H5NS+. Protonated dinitrosylated dipeptide dissociated by losing both NO molecules, forming a cyclic structure with a vicinal disulfide bridge whose major dissociation channel was the loss of CO. After CO loss, two pathways were observed (loss of NH3 and C2H3NS) which were preceded by proton exchange occurring between one β-carbon and the nitrogen atom. DFT calculations did not show significant differences in the energies involved for the loss of the NO radical from either of the cysteine residues of the protonated di-nitrosylated dipeptide. Upon loss of the first NO radical, the thiyl radical afforded the vicinal disulfide product with a small barrier through radical substitution of the remaining NO moiety. The calculated relative energy barriers for the different channels are in good agreement with experimental observations. Structures of the ions obtained after dissociation are suggested on the basis of the proposed mechanisms. © 2016 the Owner Societies. |l eng | |
| 593 | |a Department of Chemistry and Centre for Research in Mass Spectrometry, York University, 4700 Keele Street, Toronto, ON M3J 1P3, Canada | ||
| 593 | |a Department of Chemistry and Biochemistry, University of Windsor, 401 Sunset Avenue, Windsor, ON N9B 3P4, Canada | ||
| 593 | |a Departamento de Quiimica Orgainica, UMyMFOR-CONICET, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón II, 31 piso, Buenos Aires, C1428EHA, Argentina | ||
| 690 | 1 | 0 | |a CYSTEINE |
| 690 | 1 | 0 | |a CYSTEINYLCYSTEINE |
| 690 | 1 | 0 | |a DIPEPTIDE |
| 690 | 1 | 0 | |a CHEMISTRY |
| 690 | 1 | 0 | |a ELECTROSPRAY MASS SPECTROMETRY |
| 690 | 1 | 0 | |a TANDEM MASS SPECTROMETRY |
| 690 | 1 | 0 | |a THERMODYNAMICS |
| 690 | 1 | 0 | |a CYSTEINE |
| 690 | 1 | 0 | |a DIPEPTIDES |
| 690 | 1 | 0 | |a SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION |
| 690 | 1 | 0 | |a TANDEM MASS SPECTROMETRY |
| 690 | 1 | 0 | |a THERMODYNAMICS |
| 700 | 1 | |a Michael Siu, K.W. | |
| 700 | 1 | |a Hopkinson, A.C. | |
| 773 | 0 | |d Royal Society of Chemistry, 2016 |g v. 18 |h pp. 6047-6052 |k n. 8 |p Phys. Chem. Chem. Phys. |x 14639076 |t Physical Chemistry Chemical Physics | |
| 856 | 4 | 1 | |u https://www.scopus.com/inward/record.uri?eid=2-s2.0-84958972650&doi=10.1039%2fc5cp08014b&partnerID=40&md5=f295489fd47b871604cf99eee07b7076 |y Registro en Scopus |
| 856 | 4 | 0 | |u https://doi.org/10.1039/c5cp08014b |y DOI |
| 856 | 4 | 0 | |u https://hdl.handle.net/20.500.12110/paper_14639076_v18_n8_p6047_Butler |y Handle |
| 856 | 4 | 0 | |u https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14639076_v18_n8_p6047_Butler |y Registro en la Biblioteca Digital |
| 961 | |a paper_14639076_v18_n8_p6047_Butler |b paper |c PE | ||
| 962 | |a info:eu-repo/semantics/article |a info:ar-repo/semantics/artículo |b info:eu-repo/semantics/publishedVersion | ||
| 963 | |a VARI | ||
| 999 | |c 77316 | ||