Structural characterization of toxic cyclic peptides from blue-green algae by tandem mass spectrometry

Combined use of chemical degradation, derivatization, and tandem mass spectrometry for rapid structural characterization of toxic cyclic peptides from blue-green algae at the nanomole level is described. Previously, all blue-green algal toxins were thought to belong to a family of seven-residue cycl...

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Bibliographic Details
Published in:Proceedings of the National Academy of Sciences - PNAS 1989-02, Vol.86 (3), p.770-774
Main Authors: Krishnamurthy, T, Szafraniec, L, Hunt, D.F, Shabanowitz, J, Yates, J.R. III, Hauer, C.R, Carmichael, W.W, Skulberg, O, Codd, G.A, Missler, S
Format: Article
Language:English
Subjects:
AGUA POTABLE
Amino Acid Sequence
Amino acids
Aminoacids, peptides. Hormones. Neuropeptides
Analytical, structural and metabolic biochemistry
Biological and medical sciences
Cyanobacteria
CYANOPHYTA
Cyclic peptides
DEGRADATION
DETERIORO
Deuterium
DRINKING WATER
EAU POTABLE
ESPECTROSCOPIA DE MASAS
Esters
Fundamental and applied biological sciences. Psychology
Indicators and Reagents
Ions
Mass spectra
Mass Spectrometry
MASS SPECTROSCOPY
Microcystins
MICROCYSTIS AERUGINOSA
Molecular Sequence Data
Mycrocystis aeruginosa
PEPTIDE
PEPTIDES
Peptides, Cyclic - isolation & purification
PEPTIDOS
Plants, Toxic
Proteins
SPECTROGRAPHIE DE MASSE
SUBSTANCE TOXIQUE
SUBSTANCIAS TOXICAS
TOXIC SUBSTANCES
Toxicity
Toxins
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Summary:Combined use of chemical degradation, derivatization, and tandem mass spectrometry for rapid structural characterization of toxic cyclic peptides from blue-green algae at the nanomole level is described. Previously, all blue-green algal toxins were thought to belong to a family of seven-residue cyclic peptides, having the general structure cyclo-D-Ala-L-Xaa-erythro-β -methyl-D-isoaspartic acid-L-Yaa-Adda-D-isoglutamic acid-N-methyldehydroalanine, where Xaa and Yaa represent variable amino acids of the L configuration and Adda is 3-amino-9-methoxy-2,6,8-trimethyl-10-phenyldeca-4,6-dienoic acid. Structural characterization of two additional toxins indicates that further variability can exist within this family of naturally occurring toxic cyclic peptides. Isoaspartic acid and dehydroalanine can substitute for β -methylisoaspartic acid and N-methyldehydroalanine, respectively.
ISSN:0027-8424
1091-6490
DOI:10.1073/pnas.86.3.770