Structure of (-)-neodysidenin from Dysidea herbacea. Implications for biosynthesis of 5,5,5-trichloroleucine peptides

J B MacMillan; E K Trousdale; T F Molinski

doi:10.1021/ol006326u

Structure of (-)-neodysidenin from Dysidea herbacea. Implications for biosynthesis of 5,5,5-trichloroleucine peptides

Org Lett. 2000 Aug 24;2(17):2721-3. doi: 10.1021/ol006326u.

Authors

J B MacMillan¹, E K Trousdale, T F Molinski

Affiliation

¹ Department of Chemistry, University of California, Davis 95616, USA.

PMID: 10990437
DOI: 10.1021/ol006326u

Abstract

[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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Carrier Proteins / antagonists & inhibitors*
Dipeptides / biosynthesis*
Dipeptides / chemical synthesis*
Gas Chromatography-Mass Spectrometry
Membrane Proteins / antagonists & inhibitors*
Molecular Conformation
Porifera / chemistry*
Spectrometry, Mass, Fast Atom Bombardment
Symporters*
Thiazoles / chemical synthesis*

Substances

Carrier Proteins
Dipeptides
Membrane Proteins
Symporters
Thiazoles
neodysidenin
sodium-iodide symporter