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

Shibaji K. Ghosh; Brinda Somanadhan; Kevin S.W. Tan; Mark S. Butler; Martin J. Lear

doi:10.1021/ol300293a

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

Shibaji K. Ghosh, Brinda Somanadhan, Kevin S.W. Tan, Mark S. Butler, Martin J. Lear

SCI - Chemistry

Research output: Contribution to journal › Article › peer-review

14 Citations (Scopus)

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.

Original language	English
Pages (from-to)	1560-1563
Number of pages	4
Journal	Organic letters
Volume	14
Issue number	6
DOIs	https://doi.org/10.1021/ol300293a
Publication status	Published - 2012 Mar 16

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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AU - Ghosh, Shibaji K.

AU - Somanadhan, Brinda

AU - Tan, Kevin S.W.

AU - Butler, Mark S.

AU - Lear, Martin J.

PY - 2012/3/16

Y1 - 2012/3/16

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AB - 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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