Structure of (-)-neodysidenin from Dysidea herbacea. Implications for biosynthesis of 5,5,5-trichloroleucine peptides.
[structure: see text]Neodysidenin was isolated from the marine sponge Dysidea herbacea (Keller 1889) collected on the Great Barrier Reef. The complete configuration was obtained from a combination of methods, including capillary electrophoresis of Marfey's derivatives. Neodysidenin belongs to the L-series of trichloroleucine peptides, and the configuration of the N-methyl thiazolyl alanine residue (13R) is opposite to that of dysidenin.
MacMillan
J B
JB
Department of Chemistry, University of California, Davis 95616, USA.
Trousdale
E K
EK
Molinski
T F
TF
D000818:Animals; D002352:Carrier Proteins / Q000037:antagonists & inhibitors*; D004151:Dipeptides / Q000096:biosynthesis* / Q000138:chemical synthesis*; D008401:Gas Chromatography-Mass Spectrometry; D008565:Membrane Proteins / Q000037:antagonists & inhibitors*; D008968:Molecular Conformation; D011161:Porifera / Q000737:chemistry*; D016339:Spectrometry, Mass, Fast Atom Bombardment; D027981:Symporters; D013844:Thiazoles / Q000138:chemical synthesis*; D000099209:Sodium-Iodide Symporters
D002352:Carrier Proteins; D004151:Dipeptides; D008565:Membrane Proteins; D027981:Symporters; D013844:Thiazoles; D000099209:Sodium-Iodide Symporters; C414392:neodysidenin