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

11 Citations (Scopus)

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

Fingerprint

Colletotrichum trifolii
cutin
stereoisomers
Stereochemistry
stereochemistry
Chemical activation
tomatoes
synthesis
pathogens
acids
Colletotrichum
Stereoisomerism
Pathogens
Lycopersicon esculentum
Monomers
9-(2,3-dihydroxypropyl)adenine
10,16-dihydroxyhexadecanoic acid

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Plant Science
  • Horticulture

Cite this

Synthesis of (R)- and (S)-10,16-dihydroxyhexadecanoic acid : Cutin stereochemistry and fungal activation. / Ahmed, Aqeel; Crawford, Terry; Gould, Stephanie; Ha, Y. S.; Hollrah, Monica; Noor-E-Ain, Farhana; Dickman, Martin B.; Dussault, Patrick H.

In: Phytochemistry, Vol. 63, No. 1, 01.05.2003, p. 47-52.

Research output: Contribution to journalArticle

Ahmed, A, Crawford, T, Gould, S, Ha, YS, Hollrah, M, Noor-E-Ain, F, Dickman, MB & Dussault, PH 2003, 'Synthesis of (R)- and (S)-10,16-dihydroxyhexadecanoic acid: Cutin stereochemistry and fungal activation', Phytochemistry, vol. 63, no. 1, pp. 47-52. https://doi.org/10.1016/S0031-9422(03)00003-7
Ahmed, Aqeel ; Crawford, Terry ; Gould, Stephanie ; Ha, Y. S. ; Hollrah, Monica ; Noor-E-Ain, Farhana ; Dickman, Martin B. ; Dussault, Patrick H. / Synthesis of (R)- and (S)-10,16-dihydroxyhexadecanoic acid : Cutin stereochemistry and fungal activation. In: Phytochemistry. 2003 ; Vol. 63, No. 1. pp. 47-52.
@article{3c8adf60adab4bceb2af9b4857d49444,
title = "Synthesis of (R)- and (S)-10,16-dihydroxyhexadecanoic acid: Cutin stereochemistry and fungal activation",
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.",
keywords = "Asymmetric synthesis, Colletotrichum trifolii, Cutin monomers, DHPA, Dihydroxyhexadecanoic acid, Lycopersicon esculentum, Solonaceae, Tomato",
author = "Aqeel Ahmed and Terry Crawford and Stephanie Gould and Ha, {Y. S.} and Monica Hollrah and Farhana Noor-E-Ain and Dickman, {Martin B.} and Dussault, {Patrick H}",
year = "2003",
month = "5",
day = "1",
doi = "10.1016/S0031-9422(03)00003-7",
language = "English (US)",
volume = "63",
pages = "47--52",
journal = "Phytochemistry",
issn = "0031-9422",
publisher = "Elsevier Limited",
number = "1",

}

TY - JOUR

T1 - Synthesis of (R)- and (S)-10,16-dihydroxyhexadecanoic acid

T2 - Cutin stereochemistry and fungal activation

AU - Ahmed, Aqeel

AU - Crawford, Terry

AU - Gould, Stephanie

AU - Ha, Y. S.

AU - Hollrah, Monica

AU - Noor-E-Ain, Farhana

AU - Dickman, Martin B.

AU - Dussault, Patrick H

PY - 2003/5/1

Y1 - 2003/5/1

N2 - 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.

AB - 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.

KW - Asymmetric synthesis

KW - Colletotrichum trifolii

KW - Cutin monomers

KW - DHPA

KW - Dihydroxyhexadecanoic acid

KW - Lycopersicon esculentum

KW - Solonaceae

KW - Tomato

UR - http://www.scopus.com/inward/record.url?scp=0037403606&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0037403606&partnerID=8YFLogxK

U2 - 10.1016/S0031-9422(03)00003-7

DO - 10.1016/S0031-9422(03)00003-7

M3 - Article

VL - 63

SP - 47

EP - 52

JO - Phytochemistry

JF - Phytochemistry

SN - 0031-9422

IS - 1

ER -