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2006 | 4 | 4 | 620-631
Tytuł artykułu

Sequencing peptides by electrospray ion-trap mass spectrometry: A useful tool in synthesis of Axinastatin 3

Treść / Zawartość
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
Axinastatin 3 as a potential anticancer agent was synthesized by chemical methods. In an electrospray ion-trap mass spectrometer, using one stage of tandem mass spectrometry (MS/MS), the linear peptide intermediate was sequenced via the complementarities of y and b ions. Then, using multistep MS/MS (to MS6), the cyclic peptide was sequenced through sequentially removing one amino acid residue in each stage of MS/MS. The difference of the fragmentation mechanisms and the sequencing approaches between them is discussed.
Wydawca
Czasopismo
Rocznik
Tom
4
Numer
4
Strony
620-631
Opis fizyczny
Daty
wydano
2006-12-01
online
2006-12-01
Twórcy
autor
  • Chemical Engineering Research Center, School of Chemical Engineering and Technology, Tianjin University, Tianjin, 300072, People’s Republic of China
autor
  • Chemical Engineering Research Center, School of Chemical Engineering and Technology, Tianjin University, Tianjin, 300072, People’s Republic of China , qiwei@tju.edu.cn
autor
  • Chemical Engineering Research Center, School of Chemical Engineering and Technology, Tianjin University, Tianjin, 300072, People’s Republic of China
autor
  • Chemical Engineering Research Center, School of Chemical Engineering and Technology, Tianjin University, Tianjin, 300072, People’s Republic of China
Bibliografia
  • [1] J.S. Davies: “The cyclization of peptides and depsipeptides”, J. Peptide Sci., Vol. 9, (2003), pp. 471–501. http://dx.doi.org/10.1002/psc.491[Crossref]
  • [2] G.R. Pettit, F. Gao, R.L. Cerny, D.L. Doubek, L.P. Tackett, J.M. Schmidt, and J. Chapuis: “Antineoplastic agents. 278. Isolation and structure of Axinastatins 2 and 3 from a western caroline island marine sponge”, J. Med. Chem., Vol. 37, (1994), pp. 1165–1168. http://dx.doi.org/10.1021/jm00034a014[Crossref]
  • [3] B.M. Souza, M.R. Marques, D.M. Tomazela, M.N. Eberlin, M.A. Mendes and M.S. Palma: “Mass spectrometric characterization of two novel inflammatory peptides from the venom of the social wasp Polybia paulista”, Rapid Commun. Mass Spectrom., Vol. 18, (2004), pp. 1095–1102. http://dx.doi.org/10.1002/rcm.1452[Crossref]
  • [4] W. Qi, C.X. Jia, Z.M. He and B. Qiao: “Analysis of racemization products of synthetic heptapeptide by reversed phase high performance liquid chromatography/mass spectrometry”, Chinese J. Anal. Chem., in press.
  • [5] B. Paizs and S. Suhai: “Fragmentation pathways of protonated peptides”, Mass Spec. Rev., Vol. 24, (2005), pp. 508–548. http://dx.doi.org/10.1002/mas.20024[Crossref]
  • [6] V.H. Wysocki, K.A. Resing, Q.F. Zhang and G.L. Cheng: “Mass spectrometry of peptides and proteins”, Methods, Vol. 35, (2005), pp. 211–222. http://dx.doi.org/10.1016/j.ymeth.2004.08.013[Crossref]
  • [7] L.C.M. Ngoka and M.L. Gross: “Multistep tandem mass spectrometry for sequencing cyclic peptides in an ion-trap mass spectrometer”, J. Am. Soc. Mass Spectrom., Vol. 10, (1999), pp. 732–746. http://dx.doi.org/10.1016/S1044-0305(99)00049-5[Crossref]
  • [8] L.C.M. Ngoka and M.L. Gross: “A nomenclature system for labeling cyclic peptides fragments”, J. Am. Soc. Mass Spectrom., Vol. 10, (1999), pp. 360–363. http://dx.doi.org/10.1016/S1044-0305(99)00006-9[Crossref]
  • [9] L.C.M. Ngoka, M.L. Gross and P.L. Toogood: “Sodium-directed selective cleavage of lactones: a method for structure determination of cyclodepsipeptides”, Int. J. Mass Spectrom., Vol. 182/183, (1999), pp. 289–298. http://dx.doi.org/10.1016/S1387-3806(98)14248-3[Crossref]
  • [10] L.C.M. Ngoka and M.L. Gross: “Multistep collisionally activated decomposition in an ion trap for the determination of the amino-acid sequence and gas-phase ion chemistry of lithium-coordinated valinomycin”, Int. J. Mass Spectrom., Vol. 194, (2000), pp. 247–259. http://dx.doi.org/10.1016/S1387-3806(99)00192-X[Crossref]
  • [11] L.C.M. Ngoka and M.L. Gross: “Location of alkali metal binding sites in Endothelin A selective antagonists, cylco(D-Trp-D-Asp-Pro-D-Val-Leu) and cylco(D-Trp-D-Asp-Pro-D-Ile-Leu)”, J. Mass Spectrom., Vol. 35, (2000), pp. 265–276. http://dx.doi.org/10.1002/(SICI)1096-9888(200002)35:2<265::AID-JMS946>3.0.CO;2-#[Crossref]
  • [12] S.M. Williams and J.S. Brodbelt: “MSn characterization of protonated cyclic peptides and metal complexes”, J. Am. Soc. Mass Spectrom., Vol. 15, (2004), pp. 1039–1054. http://dx.doi.org/10.1016/j.jasms.2004.03.015[Crossref]
  • [13] C.X. Jia, W. Qi, Z.M. He, H.M. Yang and B. Qiao: “Synthesis of heptapeptides and analysis of sequence by tandem ion trap mass spectrometry”, Cent. Eur. J. Chem., Vol. 4, (2006), pp. 285–298. http://dx.doi.org/10.2478/s11532-006-0004-6[Crossref]
  • [14] P. Roepstorff and J. Fohlmann: “Proposal for a common nomenclature for sequence ions in mass spectra of peptides”, Biomed. Mass Spectrom., Vol. 11, (1984), pp. 601–601. http://dx.doi.org/10.1002/bms.1200111109[Crossref]
  • [15] V.H. Wysocki, G. Tsaprailis, L.L. Smith and L.A. Breci: “Mobile and localized protons: A framework for understanding peptide dissociation”, J. Mass Spectrom., Vol. 35, (2000), pp. 1399–1406. http://dx.doi.org/10.1002/1096-9888(200012)35:12<1399::AID-JMS86>3.0.CO;2-R[Crossref]
  • [16] M.J. Polce, D. Ren and C. Wesdemiotis: “Dissociation of the peptide bond in protonated peptides”, J. Mass Spectrom., Vol. 35, (2000), pp. 1391–1398. http://dx.doi.org/10.1002/1096-9888(200012)35:12<1391::AID-JMS85>3.0.CO;2-1[Crossref]
  • [17] R.S. Johnson, S.A. Martin and K. Biemann: “Collision-induced fragmentation of (M+H)+ ions of peptides. Side chain specific sequence ions”, Int. J. Mass Spectrom. Ion Processes, Vol. 86, (1988), pp. 137–154. http://dx.doi.org/10.1016/0168-1176(88)80060-0[Crossref]
  • [18] M.A. Mendes, B.M. Souza, L.D. Santos and M.S. Palma: “Structural characteriztion of novel chemotactic and mastoparan peptides from the venom of the social wasp Agelaia pallipes pallipes by high-performance liquid chromatography/electrospray ionization tandem mass spectrometry”, Rapid Commun. Mass Specrom., Vol. 18, (2004), pp. 636–642. http://dx.doi.org/10.1002/rcm.1382[Crossref]
  • [19] R.W. Vachet, B.M. Bishop, B.W. Erickson and G.L. Glish: “Novel peptide dissociation: Gas-phase intramolecular rearrangement of internal amino acid residues”, J. Am. Chem. Soc., Vol. 119, (1997), pp. 5481–5488. http://dx.doi.org/10.1021/ja9640758[Crossref]
  • [20] P. Stefanowicz: “Electrospray mass spectrometry and tandem mass spectrometry of the matural mixture of cyclic peptides from linseed”, Eur. J. Mass Spectrom., Vol. 10, (2004), pp. 665–671. http://dx.doi.org/10.1255/ejms.657[Crossref]
  • [21] B. Paizs, M. Schnolzer, U. Warnken and S. Suhai: “Cleavage of the amide bond of protonated dipeptides”, Phys. Chem. Chem. Phys., Vol. 6, (2004), pp. 2691–2699. http://dx.doi.org/10.1039/b315597h[Crossref]
Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.-psjd-doi-10_2478_s11532-006-0028-y
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