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

Research output: Contribution to journalArticlepeer-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 languageEnglish
Pages (from-to)1560-1563
Number of pages4
JournalOrganic letters
Volume14
Issue number6
DOIs
Publication statusPublished - 2012 Mar 16

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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