Synthesis and anthelmintic activity of substituted (R)-phenyllactic acid containing cyclohexadepsipeptides
| Autor: | Achim Harder, Peter Jeschke, Michael Schindler, Wolfgang Gau, Hans-Christoph Weiss, Jordi Benet-Buchholz, Winfried Etzel |
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| Rok vydání: | 2006 |
| Předmět: |
Models
Molecular Stereochemistry Protein Conformation Clinical Biochemistry Molecular Conformation Pharmaceutical Science Crystallography X-Ray Biochemistry Chemical synthesis Peptides Cyclic chemistry.chemical_compound Amide Depsipeptides Drug Discovery Side chain Animals Lactic Acid Molecular Biology Conformational isomerism chemistry.chemical_classification Anthelmintics Sheep Chemistry Organic Chemistry Total synthesis Cyclic peptide Models Chemical Lactates Molecular Medicine Enniatin Peptides Two-dimensional nuclear magnetic resonance spectroscopy |
| Zdroj: | Bioorganicmedicinal chemistry letters. 16(16) |
| ISSN: | 0960-894X |
| Popis: | 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-PhLac2). |
| Databáze: | OpenAIRE |
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