메뉴 건너뛰기




Volumn 25, Issue 5, 2014, Pages 778-789

Collision-induced dissociation of diazirine-labeled peptide ions. Evidence for Brønsted-acid assisted elimination of nitrogen

Author keywords

Collision induced dissociation; Diazirine labeled peptides; Dissociation mechanisms; Ion structures; Nitrogen elimination

Indexed keywords

AMINO ACIDS; IONS; NITROGEN; PEPTIDES; PROTONS;

EID: 84899546415     PISSN: 10440305     EISSN: 18791123     Source Type: Journal    
DOI: 10.1007/s13361-014-0832-0     Document Type: Article
Times cited : (17)

References (43)
  • 1
    • 80052252927 scopus 로고    scopus 로고
    • Design, synthesis, and photoactivation studies of fluorous photolabels
    • 10.1039/c1ob05748k
    • Kumar, A.B., Anderson, J.M., Manetsch, R.: Design, synthesis, and photoactivation studies of fluorous photolabels. Org. Biomol. Chem. 9, 6284-6292 (2011)
    • (2011) Org. Biomol. Chem. , vol.9 , pp. 6284-6292
    • Kumar, A.B.1    Anderson, J.M.2    Manetsch, R.3
  • 2
    • 53249136150 scopus 로고    scopus 로고
    • Recent progress in diazirine-based photoaffinity labeling
    • Hashimoto, M., Hatanaka, Y.: Recent progress in diazirine-based photoaffinity labeling. Eur. J. Org. Chem. 2008, 2513-2523 (2008)
    • (2008) Eur. J. Org. Chem. 2008 , pp. 2513-2523
    • Hashimoto, M.1    Hatanaka, Y.2
  • 3
    • 80051772487 scopus 로고    scopus 로고
    • Aliphatic diazirines as photoaffinity probes for proteins: Recent developments
    • 10.1021/cr1002722
    • Das, J.: Aliphatic diazirines as photoaffinity probes for proteins: recent developments. Chem. Rev. 111, 4405-4417 (2011)
    • (2011) Chem. Rev. , vol.111 , pp. 4405-4417
    • Das, J.1
  • 5
    • 0010797414 scopus 로고
    • The photolysis of dimethyldiazirine
    • doi: 10.1039/JR9630003514
    • Frey, H.M., Stevens, I.D.R.: The photolysis of dimethyldiazirine. J. Chem. Soc. 3514-3519 (1963). doi: 10.1039/JR9630003514
    • (1963) J. Chem. Soc. , pp. 3514-3519
    • Frey, H.M.1    Stevens, I.D.R.2
  • 6
    • 0000379153 scopus 로고
    • Photoisomerization of diazirine
    • 10.1021/ja01056a044
    • Amrich, M.J., Bell, J.A.: Photoisomerization of diazirine. J. Am. Chem. Soc. 86, 292-293 (1964)
    • (1964) J. Am. Chem. Soc. , vol.86 , pp. 292-293
    • Amrich, M.J.1    Bell, J.A.2
  • 7
    • 0005712641 scopus 로고
    • Comparative reactivity of methylene, carbomethoxycarbene, and dicarbethoxycarbene toward the saturated carbon-hydrogen bond
    • 10.1021/ja01469a050
    • Doering, W., von, E., Knox, L.H.: Comparative reactivity of methylene, carbomethoxycarbene, and dicarbethoxycarbene toward the saturated carbon-hydrogen bond. J. Am. Chem. Soc. 83, 1989-1992 (1961)
    • (1961) J. Am. Chem. Soc. , vol.83 , pp. 1989-1992
    • Doering, W.1    Von, E.2    Knox, L.H.3
  • 9
    • 0019332445 scopus 로고
    • 3-Trifluoromethyl-3-phenyldiazirine. A new carbene generating group for photolabeling reagents
    • Brunner, J., Senn, H., Richards, F.M.: 3-Trifluoromethyl-3- phenyldiazirine. A new carbene generating group for photolabeling reagents. J. Biol. Chem. 255, 3313-3318 (1980)
    • (1980) J. Biol. Chem. , vol.255 , pp. 3313-3318
    • Brunner, J.1    Senn, H.2    Richards, F.M.3
  • 10
    • 18744389180 scopus 로고    scopus 로고
    • Photo-leucine and photo-methionine allow identification of protein-protein interactions in living cells
    • 10.1038/nmeth752
    • Suchanek, M., Radzikowska, A., Thiele, C.: Photo-leucine and photo-methionine allow identification of protein-protein interactions in living cells. Nat. Methods 2, 261-268 (2005)
    • (2005) Nat. Methods , vol.2 , pp. 261-268
    • Suchanek, M.1    Radzikowska, A.2    Thiele, C.3
  • 11
    • 0141695631 scopus 로고
    • Mechanism of thermal decomposition of diazirine. Evidence for diazomethane intermediate
    • 10.1021/ja00436a073
    • Jennings, B.M., Liu, M.T.H.: Mechanism of thermal decomposition of diazirine. Evidence for diazomethane intermediate. J. Am. Chem. Soc. 98, 6416-6417 (1976)
    • (1976) J. Am. Chem. Soc. , vol.98 , pp. 6416-6417
    • Jennings, B.M.1    Liu, M.T.H.2
  • 12
    • 26244450433 scopus 로고
    • Thermal decomposition of phenylmethyldiazirine. Effect of solvent on product distribution
    • 10.1021/jo00441a033
    • Liu, M.T.H., Ramakrishnan, K.: Thermal decomposition of phenylmethyldiazirine. Effect of solvent on product distribution. J. Org. Chem. 42, 3450-3452 (1977)
    • (1977) J. Org. Chem. , vol.42 , pp. 3450-3452
    • Liu, M.T.H.1    Ramakrishnan, K.2
  • 13
    • 80054889137 scopus 로고    scopus 로고
    • Valence isomerization between diazo compounds and diazirines
    • Korneev, S.M.: Valence isomerization between diazo compounds and diazirines. Eur. J. Org. Chem. 2011, 6153-6175 (2011).
    • (2011) Eur. J. Org. Chem. , vol.2011 , pp. 6153-6175
    • Korneev, S.M.1
  • 14
    • 0001028164 scopus 로고
    • Uber die Valenzisomerie von Diazoverbindungen und Diazirinen
    • 10.1002/cber.19751081025
    • Voigt, E., Meier, H.: Uber die Valenzisomerie von Diazoverbindungen und Diazirinen. Chem. Berlin 108, 3326-3335 (1975)
    • (1975) Chem. Berlin , vol.108 , pp. 3326-3335
    • Voigt, E.1    Meier, H.2
  • 15
    • 84870607864 scopus 로고    scopus 로고
    • Analysis of peptide secondary structures by photactivable amino acid analogues
    • 10.1002/anie.201205308
    • Kolbel, K., Ihling, C.H., Sinz, A.: Analysis of peptide secondary structures by photactivable amino acid analogues. Angew. Chem. Int. Ed. Engl. 51, 12602-12605 (2012)
    • (2012) Angew. Chem. Int. Ed. Engl. , vol.51 , pp. 12602-12605
    • Kolbel, K.1    Ihling, C.H.2    Sinz, A.3
  • 16
    • 84883850444 scopus 로고    scopus 로고
    • Electron transfer dissociation of photolabeled peptides. Backbone cleavages compete with diazirine ring rearrangements
    • 10.1007/s13361-013-0630-0
    • Marek, A., Pepin, R., Peng, B., Laszlo, K.J., Bush, M.F., Tureček, F.: Electron transfer dissociation of photolabeled peptides. Backbone cleavages compete with diazirine ring rearrangements. J. Am. Soc. Mass Spectrom. 24, 1641-1653 (2013)
    • (2013) J. Am. Soc. Mass Spectrom. , vol.24 , pp. 1641-1653
    • Marek, A.1    Pepin, R.2    Peng, B.3    Laszlo, K.J.4    Bush, M.F.5    Tureček, F.6
  • 18
    • 0025014627 scopus 로고
    • PyBOP: A new peptide coupling reagent devoid of toxic by-product
    • 10.1016/S0040-4039(00)94371-5
    • Coste, J., LeNguyen, D., Castro, B.: PyBOP: a new peptide coupling reagent devoid of toxic by-product. Tetrahedron Lett. 31, 205-208 (1990)
    • (1990) Tetrahedron Lett. , vol.31 , pp. 205-208
    • Coste, J.1    Lenguyen, D.2    Castro, B.3
  • 19
    • 79955782522 scopus 로고    scopus 로고
    • Dipole-guided electron capture causes abnormal dissociations of phosphorylated pentapeptides
    • 10.1007/s13361-011-0083-2
    • Moss, C.L., Chung, T.W., Wyer, J.A., Nielsen, S.B., Hvelplund, P., Tureček, F.: Dipole-guided electron capture causes abnormal dissociations of phosphorylated pentapeptides. J. Am. Soc. Mass Spectrom. 22, 731-751 (2011)
    • (2011) J. Am. Soc. Mass Spectrom. , vol.22 , pp. 731-751
    • Moss, C.L.1    Chung, T.W.2    Wyer, J.A.3    Nielsen, S.B.4    Hvelplund, P.5    Tureček, F.6
  • 20
    • 34250817103 scopus 로고
    • New mixing of Hartree-Fock and local density-functional theories
    • 10.1063/1.464304
    • Becke, A.D.: New mixing of Hartree-Fock and local density-functional theories. J. Chem. Phys. 98, 1372-1377 (1993)
    • (1993) J. Chem. Phys. , vol.98 , pp. 1372-1377
    • Becke, A.D.1
  • 21
    • 43049141516 scopus 로고    scopus 로고
    • The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: Two new functionals and systematic testing of four M06-class fucntionals and 12 other functionals
    • 10.1007/s00214-007-0310-x
    • Zhao, Y., Truhlar, D.G.: The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class fucntionals and 12 other functionals. Theor. Chem. Acc. 120, 215-241 (2008)
    • (2008) Theor. Chem. Acc. , vol.120 , pp. 215-241
    • Zhao, Y.1    Truhlar, D.G.2
  • 23
    • 2942631315 scopus 로고    scopus 로고
    • Accurate reaction paths using a Hessian based predictor-corrector integrator
    • 10.1063/1.1724823
    • Hratchian, H.P., Schlegel, H.B.: Accurate reaction paths using a Hessian based predictor-corrector integrator. J. Chem. Phys. 120, 9918-9924 (2004)
    • (2004) J. Chem. Phys. , vol.120 , pp. 9918-9924
    • Hratchian, H.P.1    Schlegel, H.B.2
  • 24
    • 6944251055 scopus 로고
    • A note on an approximation treatment for many-electron systems
    • 10.1103/PhysRev.46.618
    • Møller, C., Plesset, M.S.: A note on an approximation treatment for many-electron systems. Phys. Rev. 46, 618-622 (1934)
    • (1934) Phys. Rev. , vol.46 , pp. 618-622
    • Møller, C.1    Plesset, M.S.2
  • 25
    • 0000570165 scopus 로고    scopus 로고
    • Dissociation energies and kinetics of aminopyrimidinium radicals by ab initio and density functional theory
    • Tureček, F., Wolken, J.K.: Dissociation energies and kinetics of aminopyrimidinium radicals by ab initio and density functional theory. J. Phys. Chem. A 103, 1905-1912 (1999)
    • (1999) J. Phys. Chem. A , vol.103 , pp. 1905-1912
    • Tureček, F.1    Wolken, J.K.2
  • 27
    • 2642589025 scopus 로고    scopus 로고
    • Sulfur oxyacids and radicals in the gas phase. A variable-time neutralization-photoexcitation-reionization mass spectrometric and ab initio/RRKM study
    • 10.1021/ja972602x
    • Frank, A.J., Sadílek, M., Ferrier, J.G., Tureček, F.: Sulfur oxyacids and radicals in the gas phase. A variable-time neutralization-photoexcitation-reionization mass spectrometric and ab initio/RRKM study. J. Am. Chem. Soc. 119, 12343-12353 (1997)
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 12343-12353
    • Frank, A.J.1    Sadílek, M.2    Ferrier, J.G.3    Tureček, F.4
  • 28
    • 80054794290 scopus 로고    scopus 로고
    • Protonation sites and dissociation mechanisms of t-butylcarbamates in tandem mass spectrometric assays for newborn screening
    • 10.1002/jms.1993
    • Spáčil, Z., Hui, R., Gelb, M.H., Tureček, F.: Protonation sites and dissociation mechanisms of t-butylcarbamates in tandem mass spectrometric assays for newborn screening. J. Mass Spectrom. 46, 1089-1098 (2011)
    • (2011) J. Mass Spectrom. , vol.46 , pp. 1089-1098
    • Spáčil, Z.1    Hui, R.2    Gelb, M.H.3    Tureček, F.4
  • 29
    • 84859568806 scopus 로고    scopus 로고
    • Gas phase basicities of polyfunctional molecules. Part 3: Amino acids
    • 10.1002/mas.20349
    • Bouchoux, G.L.: Gas phase basicities of polyfunctional molecules. Part 3: amino acids. Mass Spectrom. Rev. 31, 391-435 (2012)
    • (2012) Mass Spectrom. Rev. , vol.31 , pp. 391-435
    • Bouchoux, G.L.1
  • 30
    • 0035860265 scopus 로고    scopus 로고
    • Site specific sequestering and stabilization of charge in peptides by supramolecular adduct formation with 18-crown-6 ether by way of electrospray ionization
    • 10.1016/S1387-3806(01)00431-6
    • Julian, R.R., Beauchamp, J.E.: Site specific sequestering and stabilization of charge in peptides by supramolecular adduct formation with 18-crown-6 ether by way of electrospray ionization. Int. J. Mass Spectrom. 210/211, 613-623 (2001)
    • (2001) Int. J. Mass Spectrom. , vol.210-211 , pp. 613-623
    • Julian, R.R.1    Beauchamp, J.E.2
  • 32
    • 80054045344 scopus 로고    scopus 로고
    • Electron-capture induced dissociation of doubly charged dipeptides: On the neutral losses and N-Cα bond cleavages
    • 10.1039/c1cp21549c
    • Jensen, C.S., Wyer, J.A., Houmoller, J., Hvelplund, P., Nielsen, S.B.: Electron-capture induced dissociation of doubly charged dipeptides: on the neutral losses and N-Cα bond cleavages. Phys. Chem. Chem. Phys. 13, 18373-18378 (2011)
    • (2011) Phys. Chem. Chem. Phys. , vol.13 , pp. 18373-18378
    • Jensen, C.S.1    Wyer, J.A.2    Houmoller, J.3    Hvelplund, P.4    Nielsen, S.B.5
  • 33
    • 0001588558 scopus 로고    scopus 로고
    • The gas-phase basicities and proton affinities of amino acids and peptides
    • 10.1002/(SICI)1098-2787(1997)16:4<201: AID-MAS3>3.0.CO;2-L
    • Harrison, A.G.: The gas-phase basicities and proton affinities of amino acids and peptides. Mass Spectrom. Rev. 16, 201-217 (1997)
    • (1997) Mass Spectrom. Rev. , vol.16 , pp. 201-217
    • Harrison, A.G.1
  • 34
    • 21844457685 scopus 로고    scopus 로고
    • Fragmentation pathways of protonated peptides
    • 10.1002/mas.20024
    • Paizs, B., Suhai, S.: Fragmentation pathways of protonated peptides. Mass Spectrom. Rev. 24, 508-548 (2005)
    • (2005) Mass Spectrom. Rev. , vol.24 , pp. 508-548
    • Paizs, B.1    Suhai, S.2
  • 35
    • 78449244153 scopus 로고    scopus 로고
    • Effect of the basic residue on the energetics, dynamics, and mechanisms of gas-phase fragmentation of protonated peptides
    • 10.1021/ja104438z
    • Laskin, J., Yang, Z.-B., Song, T., Lam, C., Chu, I.K.: Effect of the basic residue on the energetics, dynamics, and mechanisms of gas-phase fragmentation of protonated peptides. J. Am. Chem. Soc. 132, 16006-16016 (2010)
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 16006-16016
    • Laskin, J.1    Yang, Z.-B.2    Song, T.3    Lam, C.4    Chu, I.K.5
  • 36
    • 46949102950 scopus 로고    scopus 로고
    • Where does the electron go? Electron distribution and reactivity of peptide cation-radicals formed by electron transfer in the gas phase
    • 10.1021/ja8019005
    • Tureček, F., Chen, X., Hao, C.: Where does the electron go? Electron distribution and reactivity of peptide cation-radicals formed by electron transfer in the gas phase. J. Am. Chem. Soc. 130, 8818-8833 (2008)
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 8818-8833
    • Tureček, F.1    Chen, X.2    Hao, C.3
  • 37
    • 55549118619 scopus 로고    scopus 로고
    • Hidden histidine rearrangements upon electron transfer to gas-phase peptide ions experimental evidence and theoretical analysis
    • 10.1021/ja8036367
    • Turecek, F., Jones, J.W., Towle, T., Panja, S., Nielsen, S.B., Hvelplund, P., Paizs, B.: Hidden histidine rearrangements upon electron transfer to gas-phase peptide ions. experimental evidence and theoretical analysis. J. Am. Chem. Soc. 130, 14584-14596 (2008)
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 14584-14596
    • Turecek, F.1    Jones, J.W.2    Towle, T.3    Panja, S.4    Nielsen, S.B.5    Hvelplund, P.6    Paizs, B.7
  • 38
    • 0029805733 scopus 로고    scopus 로고
    • Ion chemistry of protonated lysine derivatives
    • 10.1002/(SICI)1096-9888(199611)31:11<1237: AID-JMS416>3.0.CO;2-P
    • Yalcin, T., Harrison, A.G.: Ion chemistry of protonated lysine derivatives. J. Mass Spectrom. 31, 1237-1243 (1996)
    • (1996) J. Mass Spectrom. , vol.31 , pp. 1237-1243
    • Yalcin, T.1    Harrison, A.G.2
  • 39
    • 0000197230 scopus 로고    scopus 로고
    • Amide bond dissociation in protonated peptides. Structures of the N-terminal ionic and neutral fragments
    • 10.1016/S0168-1176(97)00044-X
    • Nold, M.J., Wesdemiotis, C., Yalcin, T., Harrison, A.G.: Amide bond dissociation in protonated peptides. Structures of the N-terminal ionic and neutral fragments. Int. J. Mass Spectrom. Ion Processes. 164, 137-153 (1997)
    • (1997) Int. J. Mass Spectrom. Ion Processes. , vol.164 , pp. 137-153
    • Nold, M.J.1    Wesdemiotis, C.2    Yalcin, T.3    Harrison, A.G.4
  • 40
    • 0031026946 scopus 로고    scopus 로고
    • Do all b2 ions have oxazolone structures? Multistage mass spectrometry and ab initio studies on protonated N-acyl amino acid methyl ester model systems
    • 10.1002/(SICI)1096-9888(199702)32:2<209: AID-JMS466>3.0.CO;2-C
    • Ambipathy, K., Yalcin, T., Leung, H.-W., Harrison, A.G.: Do all b 2 ions have oxazolone structures? Multistage mass spectrometry and ab initio studies on protonated N-acyl amino acid methyl ester model systems. J. Mass Spectrom. 32, 209-215 (1997)
    • (1997) J. Mass Spectrom. , vol.32 , pp. 209-215
    • Ambipathy, K.1    Yalcin, T.2    Leung, H.-W.3    Harrison, A.G.4
  • 41
    • 0035860166 scopus 로고    scopus 로고
    • Do all b2 ions have oxazolone structures multistage mass spectrometry and ab initio studies on protonated N-acyl amino acid methyl ester model systems
    • 10.1016/S1387-3806(01)00421-3
    • Farrugia, J.M., O'Hair, R.A.J., Reid, G.E.: Do all b2 ions have oxazolone structures? multistage mass spectrometry and ab initio studies on protonated N-acyl amino acid methyl ester model systems. Int. J. Mass Spectrom. 210/211, 71-87 (2001)
    • (2001) Int. J. Mass Spectrom. , vol.210-211 , pp. 71-87
    • Farrugia, J.M.1    O'Hair, R.A.J.2    Reid, G.E.3
  • 43
    • 84986848263 scopus 로고
    • Time-resolved appearance energies, breakdown graphs, and mass spectra: The elusive kinetic shift
    • 10.1002/mas.1280010402
    • Lifshitz, C.: Time-resolved appearance energies, breakdown graphs, and mass spectra: the elusive kinetic shift. Mass Spectrom. Rev. 1, 309-348 (1982)
    • (1982) Mass Spectrom. Rev. , vol.1 , pp. 309-348
    • Lifshitz, C.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.