Absolute configuration and total synthesis of a novel antimalarial lipopeptide by the de novo preparation of chiral nonproteinogenic amino acids

Ghosh, Shibaji K. and Somanadhan, Brinda and Tan, Kevin S.-W. and Butler, Mark S. and Lear, Martin J. (2012) Absolute configuration and total synthesis of a novel antimalarial lipopeptide by the de novo preparation of chiral nonproteinogenic amino acids. Organic Letters, 14 (6). pp. 1560-1563. ISSN 1523-7060

Full content URL: http://dx.doi.org/10.1021/ol300293a

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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. (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.

Keywords:total synthesis, antimalarial, Natural Product, Amino acids
Subjects:F Physical Sciences > F160 Organic Chemistry
Divisions:College of Science > School of Chemistry
ID Code:17103
Deposited On:16 Apr 2015 14:26

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