Absolute Configuration and Total Synthesis of a Novel Antimalarial Lipopeptide by the de Novo Preparation of Chiral Nonproteinogenic Amino Acids
journal contributionposted on 16.03.2012, 00:00 by Shibaji K. Ghosh, Brinda Somanadhan, Kevin S.-W. Tan, Mark S. Butler, Martin J. Lear
The absolute configuration (via degradation and Marfey’s derivatization studies) and the total synthesis of a novel antimalarial lipid-peptide isolated from Streptomyces sp. (IC50 = 0.8 μM, Plasmodium falciparum 3D7) is disclosed. To this end, versatile stereocontrolled routes to nonproteinogenic amino acids (via catalytic Mannich, Sharpless methods) and enantiomeric trans fatty acids (via Evans alkylation, Kocienski–Julia olefination) have been developed.
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KocienskiNovel Antimalarial LipopeptideStreptomyces spIC 500.8 μ MSharpless methodssynthesisacidChiral Nonproteinogenic Amino AcidsTheNovo PreparationMannichnonproteinogenicenantiomeric transEvans alkylationdegradationantimalarialderivatizationolefinationMarfeyconfigurationPlasmodiumTotal SynthesisAbsolute Configurationstereocontrolled routesfalciparum