title: Synthesis and anthelmintic activity of substituted (R)-phenyllactic acid containing cyclohexadepsipeptides.
abstract: The substituted (R)-phenyllactic acid containing cyclohexadepsipeptides (CHDPs) represent novel enniatin derivatives with strong in vivo activities against the parasitic nematode Haemonchus contortus Rudolphi in sheep. 2D NMR spectroscopic analysis revealed for the substituted (R)-phenyllactic acid containing CHDPs one major conformer with an unsymmetrically folded conformation lacking a cis-amide bond. A correlation between the substitution pattern and its anthelmintic activity was found. Here we report on a simple total synthetic pathway of the precursor for this particular type of CHDPs and an efficient modification of the benzylic side chain (R-PhLac(2)).
authors.affiliation: Bayer CropScience AG, Research & Development, Chemistry Insecticides, Monheim am Rhein, Germany. peter.jeschke@bayercropscience.com
authors.forename: Peter
authors.initials: P
authors.lastname: Jeschke
authors.forename: Jordi
authors.initials: J
authors.lastname: Benet-Buchholz
authors.forename: Achim
authors.initials: A
authors.lastname: Harder
authors.forename: Winfried
authors.initials: W
authors.lastname: Etzel
authors.forename: Michael
authors.initials: M
authors.lastname: Schindler
authors.forename: Wolfgang
authors.initials: W
authors.lastname: Gau
authors.forename: Hans-Christoph
authors.initials: HC
authors.lastname: Weiss
mesh_terms: D000818:Animals; D000871:Anthelmintics / Q000494:pharmacology*; D018360:Crystallography, X-Ray; D047630:Depsipeptides / Q000737:chemistry; D007773:Lactates / Q000737:chemistry*; D019344:Lactic Acid / Q000737:chemistry* / Q000494:pharmacology; D008956:Models, Chemical; D008958:Models, Molecular; D008968:Molecular Conformation; D010455:Peptides / Q000737:chemistry*; D010456:Peptides, Cyclic / Q000737:chemistry; D011487:Protein Conformation; D012756:Sheep / Q000469:parasitology*
chemical_list: D000871:Anthelmintics; D047630:Depsipeptides; D007773:Lactates; D010455:Peptides; D010456:Peptides, Cyclic; C100264:enniatins; C017648:3-phenyllactic acid; D019344:Lactic Acid