Total Structure Determination of Grassypeptolide, a New Marine Cyanobacterial Cytotoxin

A collection of the cyanobacterium Lyngbya confervoides off Grassy Key in Florida yielded grassypeptolide (1), a 31-membered macrocyclic depsipeptide with unusually high d-amino acid content, two thiazolines, and one β-amino acid. We report the rigorous 3D structure determination and conformational...

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Bibliographic Details
Published in:Organic letters 2008-03, Vol.10 (5), p.789-792
Main Authors: Kwan, Jason C, Rocca, James R, Abboud, Khalil A, Paul, Valerie J, Luesch, Hendrik
Format: Article
Language:English
Subjects:
Antineoplastic Agents - chemistry
Antineoplastic Agents - isolation & purification
Antineoplastic Agents - pharmacology
Crystallography, X-Ray
Cyanobacteria - chemistry
Depsipeptides - chemistry
Depsipeptides - isolation & purification
Depsipeptides - pharmacology
Drug Screening Assays, Antitumor
Florida
Humans
Inhibitory Concentration 50
Marine Biology
Molecular Conformation
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
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Summary:A collection of the cyanobacterium Lyngbya confervoides off Grassy Key in Florida yielded grassypeptolide (1), a 31-membered macrocyclic depsipeptide with unusually high d-amino acid content, two thiazolines, and one β-amino acid. We report the rigorous 3D structure determination and conformational analysis in solution and solid state by NMR, MS, X-ray crystallography, chemical degradation, and molecular modeling involving distance geometry and restrained molecular dynamics. Grassypeptolide (1) inhibited cancer cell growth with IC50 values from 1.0 to 4.2 μM.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol702946d