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

doi:10.1016/S0031-9422(03)00003-7

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 journal › Article › peer-review

17 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 language	English (US)
Pages (from-to)	47-52
Number of pages	6
Journal	Phytochemistry
Volume	63
Issue number	1
DOIs	https://doi.org/10.1016/S0031-9422(03)00003-7
State	Published - May 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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10.1016/S0031-9422(03)00003-7

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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.}",

note = "Funding Information: This work was supported by the NSF-REU program (SG), the Nebraska Research Initiative (PHD), and the USDA (MBD). We thank Ingrid Jordan-Thaden, Leah Sandvoss, and Jonathan Fritz for assistance with cutin isolation and monomer synthesis. ",

year = "2003",

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doi = "10.1016/S0031-9422(03)00003-7",

language = "English (US)",

volume = "63",

pages = "47--52",

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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.

N1 - Funding Information: This work was supported by the NSF-REU program (SG), the Nebraska Research Initiative (PHD), and the USDA (MBD). We thank Ingrid Jordan-Thaden, Leah Sandvoss, and Jonathan Fritz for assistance with cutin isolation and monomer synthesis.

PY - 2003/5

Y1 - 2003/5

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

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

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

M3 - Article

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AN - SCOPUS:0037403606

SN - 0031-9422

VL - 63

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JO - Phytochemistry

JF - Phytochemistry

IS - 1

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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