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

Academic Article
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Overview

authors

  • Krishnamurthy, T.
  • Szafraniec, L.
  • Hunt, D. F.
  • Shabanowitz, J.
  • Yates III, John
  • Hauer, C. R.
  • Carmichael, W. W.
  • Skulberg, O.
  • Codd, G. A.
  • Missler, S.

publication date

  • February 1989

journal

  • Proceedings of the National Academy of Sciences of the United States of America  Journal

abstract

  • 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-beta-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-phenyl-deca-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 beta-methylisoaspartic acid and N-methyldehydroalanine, respectively.

subject areas

  • Amino Acid Sequence
  • Cyanobacteria
  • Indicators and Reagents
  • Mass Spectrometry
  • Microcystins
  • Molecular Sequence Data
  • Peptides, Cyclic
  • Plants, Toxic
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Identity

PubMed Central ID

  • PMC286558

International Standard Serial Number (ISSN)

  • 0027-8424

Digital Object Identifier (DOI)

  • 10.1073/pnas.86.3.770

PubMed ID

  • 2492662
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Additional Document Info

start page

  • 770

end page

  • 774

volume

  • 86

issue

  • 3

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