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  • Title: Absolute configuration and total synthesis of a novel antimalarial lipopeptide by the de novo preparation of chiral nonproteinogenic amino acids.
    Author: Ghosh SK, Somanadhan B, Tan KS, Butler MS, Lear MJ.
    Journal: Org Lett; 2012 Mar 16; 14(6):1560-3. PubMed ID: 22390733.
    Abstract:
    The absolute configuration (via degradation and Marfey's derivatization studies) and the total synthesis of a novel antimalarial lipid-peptide isolated from Streptomyces sp. (IC(50) = 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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