메뉴 건너뛰기




Volumn 45, Issue 7, 2010, Pages 779-787

Formation of cyclic acylphosphoramidates in mass spectra of N-monoalkyloxyphosphoryl amino acids using electrospray ionization tandemmass spectrometry

Author keywords

CAPAs; Cyclic acylphosphoramidates; ESI MS; ESI MS MS; N phosphoryl amino acid

Indexed keywords

ALKALI METALS; ALKALINITY; AMINO ACIDS; ELECTROSPRAY IONIZATION; GASES; IONIZATION OF GASES; MASS SPECTROMETRY; METAL IONS; PARTICLE DETECTORS;

EID: 77954444120     PISSN: 10765174     EISSN: 10969888     Source Type: Journal    
DOI: 10.1002/jms.1768     Document Type: Article
Times cited : (19)

References (38)
  • 1
    • 33847167237 scopus 로고
    • Mechanism and catalysis of reaction of acyl phosphates. I. Nucleophilic reactions
    • G. D. Sabato, W. P. Jencks. Mechanism and catalysis of reaction of acyl phosphates. I. Nucleophilic reactions. J. Am. Chem. Soc. 1961, 83, 4393.
    • (1961) J. Am. Chem. Soc. , vol.83 , pp. 4393
    • Sabato, G.D.1    Jencks, W.P.2
  • 2
    • 0034530012 scopus 로고    scopus 로고
    • Acyl phosphate esters: Charge-directed acylation and artificial blood
    • R. Kluger. Acyl phosphate esters: charge-directed acylation and artificial blood. Synlett 2000, 12, 1708.
    • (2000) Synlett , vol.12 , pp. 1708
    • Kluger, R.1
  • 3
    • 0030424264 scopus 로고    scopus 로고
    • Aminoacyl ethyl phosphates. biomimetically activated amino acids
    • R. Kluger, X. F. Li, R. W. Loo. Aminoacyl ethyl phosphates. biomimetically activated amino acids. Can. J. Chem. 1996, 74, 2395.
    • (1996) Can. J. Chem. , vol.74 , pp. 2395
    • Kluger, R.1    Li, X.F.2    Loo, R.W.3
  • 4
    • 3342994871 scopus 로고    scopus 로고
    • Amino acid N-carboxyanhydrides: Activated peptide monomers behaving as phosphate-activating agents in aqueous solution
    • J. P. Biron, R. Pascal. Amino acid N-carboxyanhydrides: activated peptide monomers behaving as phosphate-activating agents in aqueous solution. J. Am. Chem. Soc. 2004, 126, 9198.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 9198
    • Biron, J.P.1    Pascal, R.2
  • 5
    • 0025803580 scopus 로고
    • Stereoselective, nonenzymatic, intramolecular transfer of amino acids
    • N. S. M. D. Wickramasinghe, M. P. Staves, J. C. Lacey. Stereoselective, nonenzymatic, intramolecular transfer of amino acids. Biochemistry 1991, 30, 2768.
    • (1991) Biochemistry , vol.30 , pp. 2768
    • Wickramasinghe, N.S.M.D.1    Staves, M.P.2    Lacey, J.C.3
  • 8
    • 0014688015 scopus 로고
    • Peptide formation in the presence of linear or cyclic polyphosphates
    • J. Rabinowitz, J. Flores, R. Krebsbach, G. Rogers. Peptide formation in the presence of linear or cyclic polyphosphates. Nature 1969, 224, 795.
    • (1969) Nature , vol.224 , pp. 795
    • Rabinowitz, J.1    Flores, J.2    Krebsbach, R.3    Rogers, G.4
  • 9
    • 0012749299 scopus 로고
    • The mechanism of the trimetaphosphate-induced peptide synthesis
    • N. Chung, R. Lohrmann, L. E. Orgel, J. Rabinowitz. The mechanism of the trimetaphosphate-induced peptide synthesis. Tetrahedron 1971, 27, 1205.
    • (1971) Tetrahedron , vol.27 , pp. 1205
    • Chung, N.1    Lohrmann, R.2    Orgel, L.E.3    Rabinowitz, J.4
  • 10
    • 0027754015 scopus 로고
    • Formation of dipeptide in the reaction of amino acids with cyclo-triphosphate
    • H. Inoue, Y. Baba, T. Furukawa, Y. Maeda, M. Tsuhako. Formation of dipeptide in the reaction of amino acids with cyclo-triphosphate. Chem. Pharm. Bull. 1993, 41, 1895.
    • (1993) Chem. Pharm. Bull. , vol.41 , pp. 1895
    • Inoue, H.1    Baba, Y.2    Furukawa, T.3    Maeda, Y.4    Tsuhako, M.5
  • 11
    • 0036959657 scopus 로고    scopus 로고
    • Trimetaphosphate-induced addition of aspartic acid to oligo (glutamic acid)s
    • A. Hill, L. E. Orgel. Trimetaphosphate-induced addition of aspartic acid to oligo (glutamic acid)s. Helv. Chim. Acta 2002, 85, 4244.
    • (2002) Helv. Chim. Acta , vol.85 , pp. 4244
    • Hill, A.1    Orgel, L.E.2
  • 12
    • 38349066158 scopus 로고    scopus 로고
    • α-Amino acid behaves differently from β-or γ -aminoacids as treatedbytrimetaphosphate
    • X. Gao, Y. Liu, P. X. Xu, Y. M. Cai, Y. F. Zhao. α-Amino acid behaves differently from β-or γ -aminoacids as treatedbytrimetaphosphate. Amino Acids 2008, 34, 47.
    • (2008) Amino Acids , vol.34 , pp. 47
    • Gao, X.1    Liu, Y.2    Xu, P.X.3    Cai, Y.M.4    Zhao, Y.F.5
  • 13
    • 0026358279 scopus 로고
    • Volcanic production of polyphosphates and its relevance to prebiotic evolution
    • Y. Yamagata, H. Watanabe, M. Saitoh, T. Namba. Volcanic production of polyphosphates and its relevance to prebiotic evolution. Nature 1991, 352, 516.
    • (1991) Nature , vol.352 , pp. 516
    • Yamagata, Y.1    Watanabe, H.2    Saitoh, M.3    Namba, T.4
  • 14
    • 54749157702 scopus 로고    scopus 로고
    • Production of potentially prebiotic condensed phosphates by phosphorus redox chemistry
    • M. A. Pasek, T. P. Kee, D. E. Bryant, A. A. Pavlov, J. I. Lunine. Production of potentially prebiotic condensed phosphates by phosphorus redox chemistry. Angew. Chem. Int. Ed. 2008, 47, 7918.
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 7918
    • Pasek, M.A.1    Kee, T.P.2    Bryant, D.E.3    Pavlov, A.A.4    Lunine, J.I.5
  • 15
    • 64149095162 scopus 로고    scopus 로고
    • N-Phosphorylation amino acids by trimetaphosphate in aqueous solution-learning from prebiotic synthesis
    • F.Ni, S. T. Sun, C. Huang, Y. F. Zhao. N-Phosphorylation amino acids by trimetaphosphate in aqueous solution-learning from prebiotic synthesis. Green Chem. 2009, 11, 569.
    • (2009) Green Chem. , vol.11 , pp. 569
    • Ni, F.1    Sun, S.T.2    Huang, C.3    Zhao, Y.F.4
  • 16
    • 66749135773 scopus 로고    scopus 로고
    • On the eletrophilicity of cyclic acylphosphoramidates (CAPAs) postulated as intermediates
    • F. Ni, X. Gao, Z. X. Zhao, C. Huang, Y. F. Zhao. On the eletrophilicity of cyclic acylphosphoramidates (CAPAs) postulated as intermediates. Eur. J. Org. Chem. 2009, 18, 3026.
    • (2009) Eur. J. Org. Chem. , vol.18 , pp. 3026
    • Ni, F.1    Gao, X.2    Zhao, Z.X.3    Huang, C.4    Zhao, Y.F.5
  • 17
    • 33845471401 scopus 로고
    • Negative ion production with the electrospray ion source
    • M. Yamashita, J. B. Fenn. Negative ion production with the electrospray ion source. J. Phys. Chem. 1984, 88, 4671.
    • (1984) J. Phys. Chem. , vol.88 , pp. 4671
    • Yamashita, M.1    Fenn, J.B.2
  • 18
    • 55249095084 scopus 로고    scopus 로고
    • Gas-phase peptide fragmentation: How understanding the fundamentals provides a springboard to developing new chemistry and novel proteomic tools
    • C. K. Barlow, R. A. J. O'Hair. Gas-phase peptide fragmentation: how understanding the fundamentals provides a springboard to developing new chemistry and novel proteomic tools. J. Mass Spectrom. 2008, 43, 1301.
    • (2008) J. Mass Spectrom. , vol.43 , pp. 1301
    • Barlow, C.K.1    O'Hair, R.A.J.2
  • 19
    • 67649213067 scopus 로고    scopus 로고
    • Phosphopeptide fragmentation and analysis by mass spectrometry
    • P. J. Boersema, S. Mohammed, A. J. R. Heck. Phosphopeptide fragmentation and analysis by mass spectrometry. J. Mass Spectrom. 2009, 44, 861.
    • (2009) J. Mass Spectrom. , vol.44 , pp. 861
    • Boersema, P.J.1    Mohammed, S.2    Heck, A.J.R.3
  • 20
    • 0347361588 scopus 로고    scopus 로고
    • The nature of phosphorylated chrysin-protein interactions involved in noncovalent complex formation by electrospray ionization mass spectrometry
    • X. L. Chen, L. B.Qu, T. Zhang, H. X. Liu, F. Yu, Y. Z. Yu, X. C. Liao, Y. F. Zhao. The nature of phosphorylated chrysin-protein interactions involved in noncovalent complex formation by electrospray ionization mass spectrometry. Anal. Chem. 2004, 76, 211.
    • (2004) Anal. Chem. , vol.76 , pp. 211
    • Chen, X.L.1    Qu, L.B.2    Zhang, T.3    Liu, H.X.4    Yu, F.5    Yu, Y.Z.6    Liao, X.C.7    Zhao, Y.F.8
  • 21
    • 1242299781 scopus 로고    scopus 로고
    • Sensitivity improvement of amino acids by N-terminal diisopropyloxyphosphorylation in electrospray ionization mass spectrometry
    • Y. Chen, J. C. Zhang, J. Chen, X. Y. Cao, J. Wang, Y. F. Zhao. Sensitivity improvement of amino acids by N-terminal diisopropyloxyphosphorylation in electrospray ionization mass spectrometry. Rapid Commun. Spectrom. 2004, 18, 469.
    • (2004) Rapid Commun. Spectrom. , vol.18 , pp. 469
    • Chen, Y.1    Zhang, J.C.2    Chen, J.3    Cao, X.Y.4    Wang, J.5    Zhao, Y.F.6
  • 22
    • 0034781786 scopus 로고    scopus 로고
    • Rearrangement of P-N and P-O bonds in mass spectra of N-diisopropyloxyphosphoryl amino acids/alcohols
    • J. Chen, Y. Chen, Y. Jiang, H. Fu, Y. F. Zhao. Rearrangement of P-N and P-O bonds in mass spectra of N-diisopropyloxyphosphoryl amino acids/alcohols. Rapid Commun. Spectrom. 2001, 15, 1936.
    • (2001) Rapid Commun. Spectrom. , vol.15 , pp. 1936
    • Chen, J.1    Chen, Y.2    Jiang, Y.3    Fu, H.4    Zhao, Y.F.5
  • 23
    • 19544383631 scopus 로고    scopus 로고
    • A novel rearrangement in electrospray ionization multistage tandem mass spectrometry of amino acid ester cyclohexyl phosphoramidates of AZT
    • Y. Chen, Y. W. Yin, X. B. Sun, X. H. Liu, H. Y. Wang, Y. F. Zhao. A novel rearrangement in electrospray ionization multistage tandem mass spectrometry of amino acid ester cyclohexyl phosphoramidates of AZT. J. Mass Spectrom. 2005, 40, 636.
    • (2005) J. Mass Spectrom. , vol.40 , pp. 636
    • Chen, Y.1    Yin, Y.W.2    Sun, X.B.3    Liu, X.H.4    Wang, H.Y.5    Zhao, Y.F.6
  • 24
    • 0036746749 scopus 로고    scopus 로고
    • A carbonyl oxygen migration in electrospray ionization mass spectrometry and its application in differentiating α- and β-alanyl peptides
    • J. Chen, Y. Chen, Y. Y. Niu, H. Fu, Y. F. Zhao. A carbonyl oxygen migration in electrospray ionization mass spectrometry and its application in differentiating α- and β-alanyl peptides. J. Mass Spectrom. 2002, 37, 934.
    • (2002) J. Mass Spectrom. , vol.37 , pp. 934
    • Chen, J.1    Chen, Y.2    Niu, Y.Y.3    Fu, H.4    Zhao, Y.F.5
  • 25
    • 0033585521 scopus 로고    scopus 로고
    • Oligomerization of N, O-bis(trimethylsily)-α-amino acids into peptides mediated by Ophenylene phosphorochloridate
    • H. Fu, Z. Z. Li, Y. F. Zhao, G. Z. Tu. Oligomerization of N, O-bis(trimethylsily)-α-amino acids into peptides mediated by Ophenylene phosphorochloridate. J. Am. Chem. Soc. 1999, 121, 291.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 291
    • Fu, H.1    Li, Z.Z.2    Zhao, Y.F.3    Tu, G.Z.4
  • 27
    • 33745038851 scopus 로고    scopus 로고
    • From the prebiotic synthesis of α-amino acids towards a primitive translation apparatus for the synthesis of peptides
    • R. Pascal, L. Boiteau, A. Commeyras. From the prebiotic synthesis of α-amino acids towards a primitive translation apparatus for the synthesis of peptides. Top. Curr. Chem. 2005, 259, 69.
    • (2005) Top. Curr. Chem. , vol.259 , pp. 69
    • Pascal, R.1    Boiteau, L.2    Commeyras, A.3
  • 28
    • 26844514197 scopus 로고    scopus 로고
    • Analysis of the phosphoryl transfer mechanism of c-AMP dependent protein kinase (PKA) by penta-coordinate phosphoric transition state theory
    • F. Ni, W. Li, Y. M. Li, Y. F. Zhao. Analysis of the phosphoryl transfer mechanism of c-AMP dependent protein kinase (PKA) by penta-coordinate phosphoric transition state theory. Curr. Protein Pept. Sci. 2005, 6, 437.
    • (2005) Curr. Protein Pept. Sci. , vol.6 , pp. 437
    • Ni, F.1    Li, W.2    Li, Y.M.3    Zhao, Y.F.4
  • 29
    • 33745270546 scopus 로고    scopus 로고
    • A picomole-scale method for rapid peptide sequencing through convenient and efficient N-terminal phosphorylation and electrospray ionization mass spectrometry
    • F. Wang, H. Fu, Y. Y. Jiang, Y. F. Zhao. A picomole-scale method for rapid peptide sequencing through convenient and efficient N-terminal phosphorylation and electrospray ionization mass spectrometry. J. Am. Soc. Mass Spectrom. 2006, 17, 995.
    • (2006) J. Am. Soc. Mass Spectrom. , vol.17 , pp. 995
    • Wang, F.1    Fu, H.2    Jiang, Y.Y.3    Zhao, Y.F.4
  • 30
    • 3042559633 scopus 로고    scopus 로고
    • Designing a pronucleotide stratagem: Lessons from amino acid phosphoramidated of anticancer and antiviral pyrimidines
    • D. P. Drontle, C. R. Wagner. Designing a pronucleotide stratagem: lessons from amino acid phosphoramidated of anticancer and antiviral pyrimidines. Mini-Rev. Med. Chem. 2004, 4, 409.
    • (2004) Mini-Rev. Med. Chem. , vol.4 , pp. 409
    • Drontle, D.P.1    Wagner, C.R.2
  • 31
    • 34447285964 scopus 로고    scopus 로고
    • Amino acid phosphoramidate nucleotides as alternative substrates for HIV-1 reverse transcriptase
    • O. Adelfinskaya, P. Herdewijn. Amino acid phosphoramidate nucleotides as alternative substrates for HIV-1 reverse transcriptase. Angew. Chem. Int. Ed. 2007, 46, 4356.
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 4356
    • Adelfinskaya, O.1    Herdewijn, P.2
  • 32
    • 0015915931 scopus 로고
    • Intramolecular and divalent metal ion catalysis. The hydrolytic mechanism of O-phenyl N-(glycyl)phosphoramidate
    • E. J. Sampson, J. Fedor, P. A. Benkovic, S. Benkovic. Intramolecular and divalent metal ion catalysis. The hydrolytic mechanism of O-phenyl N-(glycyl)phosphoramidate. J. Org. Chem. 1973, 38, 1301.
    • (1973) J. Org. Chem. , vol.38 , pp. 1301
    • Sampson, E.J.1    Fedor, J.2    Benkovic, P.A.3    Benkovic, S.4
  • 34
    • 0037349141 scopus 로고    scopus 로고
    • Improving hydrogen/deuterium exchange mass spectrometry by reduction of the back-exchange effect
    • M. Kipping, A. Schierhorn. Improving hydrogen/deuterium exchange mass spectrometry by reduction of the back-exchange effect. J. Mass Spectrom. 2003, 38, 271.
    • (2003) J. Mass Spectrom. , vol.38 , pp. 271
    • Kipping, M.1    Schierhorn, A.2
  • 35
    • 1442300952 scopus 로고    scopus 로고
    • Characterization of α- and γ-glutamyl dipeptides by negative ion collision-induced dissociation
    • A. G. Harrison. Characterization of α- and γ-glutamyl dipeptides by negative ion collision-induced dissociation. J. Mass Spectrom. 2004, 39, 136.
    • (2004) J. Mass Spectrom. , vol.39 , pp. 136
    • Harrison, A.G.1
  • 36
    • 0036009369 scopus 로고    scopus 로고
    • Negativei-on electrospray ionization tandem mass spectrometry of N-phosphoryl amino acids and dipeptides
    • Z. Z. Chen, S. B. Chen, Y. Chen, Y. M. Li, J. Chen, Y. F. Zhao. Negativei-on electrospray ionization tandem mass spectrometry of N-phosphoryl amino acids and dipeptides. Rapid Commun. Spectrom. 2002, 16, 790.
    • (2002) Rapid Commun. Spectrom. , vol.16 , pp. 790
    • Chen, Z.Z.1    Chen, S.B.2    Chen, Y.3    Li, Y.M.4    Chen, J.5    Zhao, Y.F.6
  • 38
    • 0041527065 scopus 로고    scopus 로고
    • Amino-catalyzed hydrolysis of amides and esters in the fragmentation by electrospray ionization tandem mass spectrometry using an ion trap
    • X. L. Yang, C. J. Zhu, S. X. Cao, X. C. Liao, Y. F. Jiang, Y. F. Zhao. Amino-catalyzed hydrolysis of amides and esters in the fragmentation by electrospray ionization tandem mass spectrometry using an ion trap. Rapid Commun. Spectrom. 2003, 17, 1927.
    • (2003) Rapid Commun. Spectrom. , vol.17 , pp. 1927
    • Yang, X.L.1    Zhu, C.J.2    Cao, S.X.3    Liao, X.C.4    Jiang, Y.F.5    Zhao, Y.F.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.