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Volumn 5, Issue 5, 1999, Pages 325-334

Neighboring group versus cis-elimination mechanisms for side chain loss from protonated methionine, methionine sulfoxide and their peptides

Author keywords

Fragmentation mechanisms; Methionine sulfoxide; Protonated peptides; Tandem mass spectrometry

Indexed keywords


EID: 0000196411     PISSN: 14690667     EISSN: None     Source Type: Journal    
DOI: 10.1255/ejms.292     Document Type: Article
Times cited : (52)

References (38)
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    • Academic Press, New York
    • For reviews on the mechanism and experimental data of gas-phase pyrolysis reactions see: (a) R.F.C. Brown, Pyrolytic Methods in Organic Chemistry. Academic Press, New York (1980), (b) G.G. Smith and F.W. Kelly, Prog. Phys. Org. Chem. 8, 75 (1971), (c) C.H. DePuy and R.W. King, Chem. Rev. 60, 431 (1960).
    • (1980) Pyrolytic Methods in Organic Chemistry
    • Brown, R.F.C.1
  • 22
    • 84982317022 scopus 로고
    • For reviews on the mechanism and experimental data of gas-phase pyrolysis reactions see: (a) R.F.C. Brown, Pyrolytic Methods in Organic Chemistry. Academic Press, New York (1980), (b) G.G. Smith and F.W. Kelly, Prog. Phys. Org. Chem. 8, 75 (1971), (c) C.H. DePuy and R.W. King, Chem. Rev. 60, 431 (1960).
    • (1971) Prog. Phys. Org. Chem. , vol.8 , pp. 75
    • Smith, G.G.1    Kelly, F.W.2
  • 23
    • 0039277875 scopus 로고
    • For reviews on the mechanism and experimental data of gas-phase pyrolysis reactions see: (a) R.F.C. Brown, Pyrolytic Methods in Organic Chemistry. Academic Press, New York (1980), (b) G.G. Smith and F.W. Kelly, Prog. Phys. Org. Chem. 8, 75 (1971), (c) C.H. DePuy and R.W. King, Chem. Rev. 60, 431 (1960).
    • (1960) Chem. Rev. , vol.60 , pp. 431
    • DePuy, C.H.1    King, R.W.2
  • 24
    • 85005669425 scopus 로고
    • For ab initio calculations on cis-1,2 eliminations see: (a) S. Wolfe and C.K. Kim, Isr. J. Chem. 33, 295 (1993), (b) B. Jursic, J. Mol. Struct. (Theochem) 389, 257 (1997).
    • (1993) Isr. J. Chem. , vol.33 , pp. 295
    • Wolfe, S.1    Kim, C.K.2
  • 25
    • 0001529764 scopus 로고    scopus 로고
    • For ab initio calculations on cis-1,2 eliminations see: (a) S. Wolfe and C.K. Kim, Isr. J. Chem. 33, 295 (1993), (b) B. Jursic, J. Mol. Struct. (Theochem) 389, 257 (1997).
    • (1997) J. Mol. Struct. (Theochem) , vol.389 , pp. 257
    • Jursic, B.1
  • 27
    • 0029915410 scopus 로고    scopus 로고
    • For previous studies suggesting the involvement of the sulfur atom in neighbouring group fragmentations of protonated methionine-containing peptides see: (a) N.N. Dookeran, T. Yalcin and A.G. Harrison, J. Mass Spectrom. 31, 500 (1996), (b) D.G. Morgan and M.M. Bursey, J. Mass Spectrom. 30, 290 (1995), (c) Y.P. Tu and A.G. Harrison, Rapid Commun. Mass Spectrom. 12, 849 (1998).
    • (1996) J. Mass Spectrom. , vol.31 , pp. 500
    • Dookeran, N.N.1    Yalcin, T.2    Harrison, A.G.3
  • 28
    • 0028945810 scopus 로고
    • For previous studies suggesting the involvement of the sulfur atom in neighbouring group fragmentations of protonated methionine-containing peptides see: (a) N.N. Dookeran, T. Yalcin and A.G. Harrison, J. Mass Spectrom. 31, 500 (1996), (b) D.G. Morgan and M.M. Bursey, J. Mass Spectrom. 30, 290 (1995), (c) Y.P. Tu and A.G. Harrison, Rapid Commun. Mass Spectrom. 12, 849 (1998).
    • (1995) J. Mass Spectrom. , vol.30 , pp. 290
    • Morgan, D.G.1    Bursey, M.M.2
  • 29
    • 0031805343 scopus 로고    scopus 로고
    • For previous studies suggesting the involvement of the sulfur atom in neighbouring group fragmentations of protonated methionine-containing peptides see: (a) N.N. Dookeran, T. Yalcin and A.G. Harrison, J. Mass Spectrom. 31, 500 (1996), (b) D.G. Morgan and M.M. Bursey, J. Mass Spectrom. 30, 290 (1995), (c) Y.P. Tu and A.G. Harrison, Rapid Commun. Mass Spectrom. 12, 849 (1998).
    • (1998) Rapid Commun. Mass Spectrom. , vol.12 , pp. 849
    • Tu, Y.P.1    Harrison, A.G.2
  • 30
    • 0003540874 scopus 로고
    • CRC Press, Boca Raton
    • For solution-phase reactions in which the sulfoxide acts as a neighbouring group see: (a) S. Oae, Organic Sulfur Chemistry: Structure and Mechanism. CRC Press, Boca Raton, p. 62 (1991), for solution phase reactions in which a protonated sulfoxide loses water via attack from a neighbouring group see: (b) Reference 10a, p. 155.
    • (1991) Organic Sulfur Chemistry: Structure and Mechanism , pp. 62
    • Oae, S.1
  • 31
    • 5844304193 scopus 로고    scopus 로고
    • Reference 10a, p. 155
    • For solution-phase reactions in which the sulfoxide acts as a neighbouring group see: (a) S. Oae, Organic Sulfur Chemistry: Structure and Mechanism. CRC Press, Boca Raton, p. 62 (1991), for solution phase reactions in which a protonated sulfoxide loses water via attack from a neighbouring group see: (b) Reference 10a, p. 155.
  • 32
    • 5844250466 scopus 로고    scopus 로고
    • -1, see J.K. Kim, J. Bonicamp and M.C. Caserio, J. Org. Chem. 46, 4230 (1981).
  • 37
    • 0029823590 scopus 로고    scopus 로고
    • + see: (a) R. A. J. O'Hair, S. Blanksby, M.L. Styles and J.H. Bowie, Int. J. Mass Spectrom. 182/183, 203 (1999), (b) M.A. Freitas, R.A.J. O'Hair, J.A.R. Schmidt, S.E. Tichy, B.E. Plashko and T.D. Williams, J. Mass Spectrom. 31, 1086 (1996).
    • (1999) Int. J. Mass Spectrom. , vol.182-183 , pp. 203
    • O'Hair, R.A.J.1    Blanksby, S.2    Styles, M.L.3    Bowie, J.H.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.