Biosynthetic origin of the 3-amino-2,5,7,8-tetrahydroxy-10-methylundecanoic acid moiety and absolute configuration of pahayokolides A and B

J Nat Prod. 2011 Jun 24;74(6):1535-8. doi: 10.1021/np200362q. Epub 2011 Jun 8.


Pahayokolides A and B are cyclic undecapeptides that were isolated from the cyanobacterium Lyngbya sp. They contain the unusual α-hydroxy-β-amino acid 3-amino-2,5,7,8-tetrahydroxy-10-methylundecanoic acid (Athmu). The absolute configurations of the amino acids of the pahayokolides, except for the four oxygen-bearing stereocenters of Athmu, have been determined by Marphy's method. Incorporation of labeled leucine and acetate precursors into the pahayokolides has established that Athmu is derived from a leucine or α-keto isocaproic acid starter unit, which is further extended with three acetate units.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Cyanobacteria / chemistry
  • Fatty Acids / biosynthesis
  • Fatty Acids / chemistry*
  • Lyngbya Toxins / chemistry*
  • Molecular Structure
  • Peptides, Cyclic / chemistry
  • Peptides, Cyclic / isolation & purification*


  • 3-amino-2,5,7,8-tetrahydroxy-10-methylundecanoic acid
  • Fatty Acids
  • Lyngbya Toxins
  • Peptides, Cyclic
  • pahayokolide A
  • pahayokolide B