Differentiation of three pairs of Boc-β,γ- and γ,β-hybrid peptides by electrospray ionization tandem mass spectrometry

Journal of Mass Spectrometry

Volumn 43, Issue 9, 2008, Pages 1201-1214

  Ramesh, V ^a   Srinivas, R ^a   Sharma, G V M ^a   Jayaprakash, P ^a   Kunwar, A C ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Carbopeptides; Electrospray ionization; Negative ion ESI; Positional and diastereo isomers; Tandem mass spectrometry

Indexed keywords

AMINES; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY;

CARBOPEPTIDES; ELECTRO SPRAYING; HYBRID PEPTIDES; NEGATIVE ION ESI; NEW SERIES; POSITIONAL AND DIASTEREO ISOMERS; TANDEM MASS SPECTROMETRY;

ELECTROSPRAY IONIZATION;

CARBOPEPTIDE; DIPEPTIDE; HEXAPEPTIDE; SYNTHETIC PEPTIDE; TETRAPEPTIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; DIASTEREOISOMER; ELECTROSPRAY MASS SPECTROMETRY; ISOMER; MASS SPECTROMETER; MASS SPECTROMETRY; MOLECULE; PEPTIDE ANALYSIS; PRIORITY JOURNAL; TANDEM MASS SPECTROMETRY; TIME OF FLIGHT MASS SPECTROMETRY;

ISOMERISM; OLIGOPEPTIDES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 52649097892     PISSN: 10765174     EISSN: 10969888     Source Type: Journal    
DOI: 10.1002/jms.1393     Document Type: Article

References (42)

1. Seebach D, Matthews JL. β-peptides: a surprise at every turn. Chemical Communications 1997; 2015.
2. DeGrado WF, Schneider JP, Hamuro Y. The twists and turns of β-peptides. Journal of Peptide Research 1999;54: 206.
3. Cheng RP, Gellman SH, DeGrado WF. β-peptides: from structure to function. Chemical Reviews 2001;101: 3219.
4. Dado GP, Gellman SH. Intramolecular hydrogen bonding in derivatives of β-alanine and λ-amino butyric acid; model studies for the folding of unnatural polypeptide backbones. Journal of the American Chemical Society 1994;116: 1054.
5. 2,3,4-peptides. Chemical Communications 2001; 207.
6. Hanessian S, Luo X, Schaum R, Michnick S. Design of secondary structures in unnatural peptides: stable helical λ-tetra-, hexa-, and octa peptides and consequences of α-substitution. Journal of the American Chemical Society 1998;120: 8569.
7. 1,2. Journal of the American Chemical Society 2004;126: 6048.
8. Vasudev PG, Shamala N, Ananda K, Balaram P. C9 helices and ribbons in λ-peptides: crystal structures of gabapentin oligomers. Angewandte Chemie International Edition 2005;44: 4972.
9. Seebach D, Overhand M, Kuhnle FNM, Martinoni B, Oberer L, Hommel U, Wildmer H. β-peptides: synthesis by Arndt-Eistern homologation with concomitant peptide coupling, structure determination by NMR and CD spectroscopy and by x-ray crystallography, helical secondary structure of a β-hexa peptide in solution and its stability towards pepsin. Helvetica Chimica Ada 1996;79: 913.
10. Appella DH, Christianson LA, Karle IL, Powell DR, Gell-man SH. β-peptide foldamers: robust helix formation in a new family of β-amino acid oligomers. Journal of the American Chemical Society 1996;118: 13071.
11. 3-peptides with proteinaceous side chains: synthesis and solution structures of constitutional isomers, a novel helical secondary structre and the influence of solvation and hydrophobic interactions on folding. Helvetica Chimica Acta 1998;81: 932.
12. Sharma GVM, Reddy KR, Krishna PR, Shankar AR, Nar-simulu K, Kumar SK, Prakash PJ, Jagannath B, Kunwar AC. Robust mixed 10/12 helices promoted by "alternating chiral-ity" in a new family of c-linked carbo-β-peptides. Journal of the American Chemical Society 2003;125:13670.
13. Sharma GVM, Reddy KR, Krishna PR, Shankar AR, Nar-simulu K, Kumar SK, Prakash PJ, Jagannath B, Kunwar AC. Left-handed helical twists in "mixed-β-peptides" derived from alternating c-linked carbo-β-amino acids and β-hGly units. Angewandte Chemie International Edition 2004;43: 3961.
14. Sharma GVM, Reddy GV, Chander VS, Reddy KR. Tetra-n-butylammonium fluoride: an efficient base for aza-michael addition synthesis of glycosyl-β-amino acid esters. Tetrahedron: Asymmetry 2002;13: 21.
15. 4-amino acids and λ-aminobutyric acid. Angewandte Chemie International Edition 2006;45: 2944.
16. Sharma GVM, Jadhav VB, Ramakrishna KVS, Jayaprakash P, Narsimulu K, Subash V, Kunwar AC. Novel 12/10- and 11/13-mixed helices in α/λ- and β/λ- hybrid peptides containing c-linked carbo-λ-amino acids with alternating α- and β-amino acids. Journal of the American Chemical Society 2006;128: 14657.
17. Biemann K. Laying the groundwork for proteomics: mass spectrometry from 1958 to 1988. International Journal of Mass Spectrometry 2007;259: 1.
18. Roepstorff P, Fohlman J. Proposal for a common nomenclature for sequence ions in mass spectra of peptides. Biomedical Mass Spectrometry 1984;11: 601.
19. Biemann K. Contribution of mass spectrometry to peptide and protein structure. Biomedical and Environmental Mass Spectrometry 1988;16: 99.
20. Biemann K. Primary studies of peptides and proteins. In Biological Mass Spectrometry: Present and Future, Matsuo T, Caprioli RM, Gross ML, Seyama T (eds). John Wiley & Sons: New York, 1993; 275.
21. McLafferty FW (ed). Tandem Mass Spectrometry. Wiley: New York, 1983.
22. Busch KL, Glish GL, McLuckeySA (eds). Mass Spectrome-try/Mass Spectrometry: Techniques and Applications of Tandem Mass spectrometry. VCH: New York, 1988.
23. Papayannopoulos IA. The interpretation of collision-induced dissociation tandem mass spectra of peptides. Mass Spectrometry Reviews 1995;14: 49.
24. Kinter M,Sherman NE. Protein Sequencing and Identification Using Tandem Mass Spectrometry. Wiley-mterscience: New York, 2000.
25. Paizs B, Suhai S. Fragmentation pathways of protonated peptides. Mass Spectrometry Reviews 2005;24: 508.
26. Waugh RJ, Bowie JH. A review of the collision-induced dissociation of deprotonated dipeptides and tripeptides. An aid to structure determination. Rapid Communications in Mass Spectrometry 1994;8: 169.
27. Harrison AG. Sequence-specific fragmentation of deprotonated containing H or alkyl side chains. Journal of the American Society for Mass Spectrometry 2001;12: 1.
28. Brinkworth CS, Dua S, McAnoy AM, Bowie JH. Negative ion fragmentations of deprotonated peptides: backbone cleavage directed through both Asp and Glu. Rapid Communications in Mass Spectrometry 2001;15:1965.
29. Boontheung P, Alewood PF; Brinkworth CS, Bowie JH, Wabnith PA, Tyler MJ. Negative ion electrospray mass spectra of caerulein peptides: an aid to structural determination. Rapid Communications in Mass Spectrometry 2002;16: 281.
30. - parent ions of underivatized peptides: an aid to structure determination and some unusual negative ion cleavages. Mass Spectrometry Reviews 2002;21: 87.
31. Clipston NL, Jai-nhuknan J, Cassady CJ. A comparison of negative and positive ion time-of-flight post-source decay mass spectrometry for peptides containing basic residues. International Journal of Mass Spectrometry 2003;222: 363.
32. Yoshida T, Tanaka K, Ido Y, Akita S, Yoshida K. Detection of high mass molecular ions by laser desorption time-of-flight mass spectrometry (in Japanese). Shitsuryo - Bunseki (Mass Spectrometry) 1988;36: 59.
33. Karas M, Hillenkamp F. Laser desorption ionization of proteins with molecular masses exceeding 10,000 daltons. Analytical Chemistry 1988;60: 2299.
34. 3-peptides: differentiation of two pairs of positional and diastereomeric isomers. Journal of Mass Spectrometry 2004;39: 1068.
35. Reddy PN, Srikanth R, Swamy NS, Srinivas R, SharmaGVM, Nagendar P, Krishna PR. Differentiation of boc-α,β- and β,α.-peptides and a pair of diastereomeric β, α-dipeptides by positive and negative ion electrospray tandem mass spectrometry. Journal of Mass Spectrometry 2005;40: 1429.
36. 3-dipeptides containing galactose, xylose and mannose sugars by electrospray ionization tandem mass spectrometry. International Journal of Mass Spectrometry 2006;248:115.
37. 4caa-1-ala: differentiation of some positional isomeric peptides. Journal of the American Society for Mass Spectrometry 2007;18: 651.
38. 3-h-valine- phenylalnine by electrospray ionization tandem mass spectrometry. Rapid Communications in Mass Spectrometry 2007;21: 1401.
39. Talaty ER, Cooper TJ, Osburn S, Van Stipdonk MJ. Collision-induced dissociation of protonated tetrapeptides containing β-alanine, λ-aminobutyric acid, ε -aminocaproic acid or 4-aminomcthylbenzoic acid residues. Rapid Communications in Mass Spectrometry 2006;20: 3443.
40. Schreiber JV, Quadroni M, Seebach D. Sequencing of β-peptides by mass spectrometry. Chimia 1999;53: 621.
41. Takayama M, Tsugita A. Sequence information of peptides and proteins with in-source decay in matrix assisted laser desorption/ioni/ation time-of-flight mass spectrometry. Electrophorcsis 2000;21: 1670.
42. Zubarev RA, Horn DM, Fridriksson EK, Kelleher NL, Kruger NA, Lewis MA, Carpenter BK, McLafferty FW. Electron capture dissociation for structural characterization of multiply charged protein cations. Analytical Chemistry 2000;72: 563.