Document Detail

Total structure determination of grassypeptolide, a new marine cyanobacterial cytotoxin.
MedLine Citation:
PMID:  18220404     Owner:  NLM     Status:  MEDLINE    
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 beta-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 microM.
Jason C Kwan; James R Rocca; Khalil A Abboud; Valerie J Paul; Hendrik Luesch
Related Documents :
22988974 - Interactions between α-tocopherol and rosmarinic acid and its alkyl esters in emulsion...
23376564 - Effect of the chemical specificity of benzoic acid and its analogues on osmotic fragili...
23663204 - Spectroscopy of protonated tetraphenylporphyrins with amino/carbomethoxy substituents: ...
24064734 - Altitudinal variation of antioxidant components and capability in indocalamus latifoliu...
7252504 - Decreases in amino acids and acetylcholine metabolism during hypoxia.
7931364 - L-741,494, a fungal metabolite that is an inhibitor of interleukin-1 beta converting en...
Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, Non-P.H.S.     Date:  2008-01-26
Journal Detail:
Title:  Organic letters     Volume:  10     ISSN:  1523-7060     ISO Abbreviation:  Org. Lett.     Publication Date:  2008 Mar 
Date Detail:
Created Date:  2008-02-28     Completed Date:  2008-05-15     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  100890393     Medline TA:  Org Lett     Country:  United States    
Other Details:
Languages:  eng     Pagination:  789-92     Citation Subset:  IM    
Department of Medicinal Chemistry, University of Florida, Gainesville, Florida 32610, USA.
Export Citation:
APA/MLA Format     Download EndNote     Download BibTex
MeSH Terms
Antineoplastic Agents / chemistry,  isolation & purification*,  pharmacology*
Crystallography, X-Ray
Cyanobacteria / chemistry*
Depsipeptides / chemistry,  isolation & purification*,  pharmacology*
Drug Screening Assays, Antitumor
Inhibitory Concentration 50
Marine Biology
Molecular Conformation
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Reg. No./Substance:
0/Antineoplastic Agents; 0/Depsipeptides; 0/grassypeptolide

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

Previous Document:  Copper-catalyzed coupling of hydroxylamines with aryl iodides.
Next Document:  Efficient short step synthesis of Corey's tamiflu intermediate.