Synthesis of (R)- and (S)-10,16-dihydroxyhexadecanoic acid: Cutin stereochemistry and fungal activation

Aqeel Ahmed, Terry Crawford, Stephanie Gould, Y. S. Ha, Monica Hollrah, Farhana Noor-E-Ain, Martin B. Dickman, Patrick H. Dussault

Research output: Contribution to journalArticle

12 Scopus citations

Abstract

The first asymmetric syntheses of the cutin monomers (R)- and (S)-10,16-dihydroxyhexadecanoic acid (10,16-DHPA) and confirmation of (S)(+)-absolute configuration for 10, 16-DHPA derived from tomato are reported. The individual DHPA stereoisomers display differences in their ability to activate the fungal pathogen Colletotrichum trifolii.

Original languageEnglish (US)
Pages (from-to)47-52
Number of pages6
JournalPhytochemistry
Volume63
Issue number1
DOIs
StatePublished - May 1 2003

Keywords

  • Asymmetric synthesis
  • Colletotrichum trifolii
  • Cutin monomers
  • DHPA
  • Dihydroxyhexadecanoic acid
  • Lycopersicon esculentum
  • Solonaceae
  • Tomato

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Plant Science
  • Horticulture

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