Document Detail


Synthesis and anthelmintic activity of cyclohexadepsipeptides with (S,S,S,R,S,R)-configuration.
MedLine Citation:
PMID:  12951110     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
The (S,S,S,R,S,R)-configurated cyclohexadepsipeptides (CHDPs) represent novel enniatin derivatives with strong in vivo activity against the parasitic nematode Haemonchus contortus Rudolphi in sheep. 2D NMR spectroscopic analysis revealed for the major conformation the asymmetric conformer, containing a cis-amide bond between C(alpha) protons of neighbouring 2-hydroxy-(S)-carboxylic acid and N-methyl-(S)-amino acid. The absolute configuration of the novel CHDPs was determined by X-ray crystallography. A correlation between the major conformer and its anthelmintic activity was found. Here, we report on a simple total synthetic pathway for this particular type of CHDPs.
Authors:
Peter Jeschke; Jordi Benet-Buchholz; Achim Harder; Winfried Etzel; Michael Schindler; Gerhard Thielking
Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Bioorganic & medicinal chemistry letters     Volume:  13     ISSN:  0960-894X     ISO Abbreviation:  Bioorg. Med. Chem. Lett.     Publication Date:  2003 Oct 
Date Detail:
Created Date:  2003-09-02     Completed Date:  2004-05-03     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9107377     Medline TA:  Bioorg Med Chem Lett     Country:  England    
Other Details:
Languages:  eng     Pagination:  3285-8     Citation Subset:  IM    
Affiliation:
Bayer CropScience AG, Research Monheim, Global Chemistry Insecticides, Building Q18, D-51368 Leverkusen, Germany. peter.jeschke@bayercropscience.com
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MeSH Terms
Descriptor/Qualifier:
Animals
Anthelmintics / chemical synthesis*,  pharmacology*
Haemonchus / drug effects*,  growth & development
Peptides, Cyclic / chemical synthesis*,  pharmacology*
Sheep
Stereoisomerism
Chemical
Reg. No./Substance:
0/Anthelmintics; 0/Peptides, Cyclic

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


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