Three novel anabaenopeptins from the cyanobacterium Anabaena sp.

Olga Grach-Pogrebinsky, Shmuel Carmeli*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

Three new cyclic peptides, anabaenopeptins NZ825, NZ841, and NZ857, were isolated from the hydrophilic extract of the cultured cyanobacterium Anabaena sp. The planar structure of the compounds was determined by homonuclear and inverse-heteronuclear 2D-NMR techniques as well as high-resolution mass spectrometry. The absolute configuration of the asymmetric centers was studied using Marfey's method for HPLC. This is the first report of anabaenopeptins that contain N-methyl glycine instead of the common N-methyl alanine. The incorporation of N-methyl glycine into the cyclic portion of the compounds results in their appearance as a mixture of two, equally stable, conformers, instead of the one distinct conformer in anabaenopeptins that contain N-methyl alanine or N-methyl homotyrosine. The three compounds were tested for inhibition of serine proteases and found to be not active.

Original languageEnglish
Pages (from-to)10233-10238
Number of pages6
JournalTetrahedron
Volume64
Issue number44
DOIs
StatePublished - 27 Oct 2008

Keywords

  • Anabaena
  • Cyanobacteria
  • Natural products

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