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

Ghosh, Shibaji K., Somanadhan, Brinda, Tan, Kevin S.-W., 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: 1560-1563.


Author Ghosh, Shibaji K.
Somanadhan, Brinda
Tan, Kevin S.-W.
Butler, Mark S.
Lear, Martin J.
Title Absolute configuration and total synthesis of a novel antimalarial lipopeptide by the de novo preparation of chiral nonproteinogenic amino acids
Journal name Organic Letters  (ERA 2012 Listed)    (ERA 2010 Rank A*)   Check publisher's open access policy
Publication date 2012-03
Sub-type Article
DOI 10.1021/ol300293a
Volume number 14
Issue number 6
ISSN 1523-7060; 1523-7052
Start page 1560
End page 1563
Total pages 4
Place of publication Washington, DC, United States
Publisher American Chemical Society
Collection year 2013
Language eng
Formatted 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.
Keyword Oxidation
Aldehydes
Alcohols
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article
Collections: Official 2013 Collection
Institute for Molecular Bioscience - Publications
 
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