Sagittamides A and B. Polyacetoxy long-chain acyl amino acids from a didemnid ascidian.
[structure: see text]. An unidentified tunicate from Pohnpei, Micronesia, yielded sagittamides A and B-compounds comprising a long-chain C26 dicarboxylic acid that acylates terminal L-valine and L-ornithine groups. The structures, which contain an unprecedented internal O-hexacetyl-1,2,3,4,5,6-hexaol moiety, were determined by combined spectroscopic analysis including mass spectrometry and 1D and 2D NMR and chemical degradation. The partial absolute stereochemistry of the new compounds was addressed by Marfey's analysis.
Lievens
Sarah C
SC
Department of Chemistry, University of California, Davis, California 95616, USA.
Molinski
Tadeusz F
TF
D000818:Animals; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D009952:Ornithine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D013237:Stereoisomerism; D014561:Urochordata / Q000737:chemistry*; D014633:Valine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology
C508005:sagittamide A; C508006:sagittamide B; D009952:Ornithine; D014633:Valine