Summary
A series of six tetrapeptides, analogues of AS-I phytotoxin, pathogenic to sunflower, have been synthesized either in solution and/or by solid phase methods and have been tested for phytotoxic activity in various plants and cytotoxic activity in three cancer cell lines. These peptides were identified as model compounds by fast atom bombardment (FAB), plasma desorption (PD), electrospray ionization (ESI) mass spectrometry and by1H,1H-1H,13C and1H-13C NMR. The data presented show that in protected tetrapeptides the molecular ion was easily identified whereas some difficulties appeared with the fully deprotected peptides. NMR spectra are given.
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References
Aberth W, Straub KM, Burlingame AL (1982) Secondary ion mass spectrometry with cesium ion primary beam and liquid target matrix for analysis of bioorganic compounds. Anal Chem 54: 2029–2034
Barber M, Bordoli RS, Garner GV, Gordon DB, Sedgwick RD, Tetler LW, Tyler AN (1981) Fast atom bombardment mass spectrometry. Spectra of enkephalins. Biochem J 197: 401–404
Barber M, Bordoli RS, Elliot GJ, Sedgwick RD, Tyler AN (1982) Fast atom bombardment mass spectrometry. Anal Chem 54: 645A-646A
Biemann K (1988) Contributions of mass spectrometry to peptide and protein structure. Biom and Envir Mass Spect 16: 99–111
Hakansson P, Sundqvist BUR (1989) Electronic sputtering of biomolecules and it's application in mass spectroscopy. Vacuum 39: 397–399
Hoppiliard Y, Mauriac C (1993) Analysis of amino acid mixtures by plasma desorption mass spectrometry. Organic Mass Spectrometry 28: 977–982
Kessler H, Gehrke M, Griesinger C (1988) Two-dimensional NMR spectroscopy: Background and overview of the experiments. Angew Chem Int Ed Eng 100: 507–554
Liakopoulou-Kyriakides M, Lagopodi AL, Thanassoulopoulos CC, Stavropoulos G, Magafa V (1997) Isolation and synthesis of a host-selective toxin produced byAlternaria alternata. Phytochemistry 45: 37–40
Liakopoulou-Kyriakides M, Metaxas A, Sarigiannis Y, Magafa V, Stavropoulos G, Laidou I, Thanassoulopoulos CC (1998) Analogues of Ser-Val-Gly-Glu (AS-I), toxin pathogenic to sunflower. Biological activities. Journal of Phytopathology 146: 279–282
Macfarlane RD, Torgerson DF (1976) Californium-252 Plasma desorption mass spectroscopy. Science 191: 920–925
Magafa V, Stavropoulos G, Tsiveriotis P, Hadjiliadis N (1998) Interaction of Hg (II) with tetrapeptides containing cysteinyl and histidyl residues. Inorg Chim Acta 272: 7–17
Magee CW (1983) Splattering of organic molecules. Int J Mass Spec Ion Phys 49: 211–221
Roepstorff P (1989) Plasma desorption mass spectrometry of peptides and proteins. Acc Chem Res 22: 421–427
Roepstorff P (1990) Methods in enzymology. In: McCloskey JA (ed) Mass spectrometry. vol 193 Academic Press, San Diego p 432
Roepstorff P, Fohlmann F (1984) Proposal for a common nomenclature for sequence ions in mass spectra of peptides. Biom and Envir Mass Spect 11: 601–602
Roepstorff P, Talbo G, Klarskov K, Hojrup P (1990) Biological mass spectrometry. In: Burlingame A, McCloskey JA (eds) Elsevier, Amstredam
Stoll R, Rollgen FW (1982) Cationization by alkali ion attachment in laser desorption mass spectrometry. Z Naturforsch 37A: 9–14
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Magafa, V., Stavropoulos, G., Aaberg, A. et al. Spectral analysis of a series of partially protected and deprotected tetrapeptides, analogues of AS-I phytotoxin. Amino Acids 16, 403–413 (1999). https://doi.org/10.1007/BF01388179
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DOI: https://doi.org/10.1007/BF01388179