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.
authors.affiliation: Department of Chemistry, University of Nebraska-Lincoln, Lincoln, NE 68588, USA.
authors.forename: Aqeel
authors.initials: A
authors.lastname: Ahmed
authors.forename: Terry
authors.initials: T
authors.lastname: Crawford
authors.forename: Stephanie
authors.initials: S
authors.lastname: Gould
authors.forename: Y S
authors.initials: YS
authors.lastname: Ha
authors.forename: Monica
authors.initials: M
authors.lastname: Hollrah
authors.forename: Farhana
authors.initials: F
authors.lastname: Noor-E-Ain
authors.forename: Martin B
authors.initials: MB
authors.lastname: Dickman
authors.forename: Patrick H
authors.initials: PH
authors.lastname: Dussault
mesh_terms: D015152:Blotting, Northern; D002265:Carboxylic Ester Hydrolases / Q000378:metabolism; D020231:Colletotrichum / Q000187:drug effects* / Q000235:genetics / Q000378:metabolism; D004789:Enzyme Activation; D015966:Gene Expression Regulation, Fungal / Q000187:drug effects; D018551:Solanum lycopersicum / Q000737:chemistry; D008563:Membrane Lipids / Q000737:chemistry*; D010169:Palmitic Acids / Q000138:chemical synthesis / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D011494:Protein Kinases / Q000378:metabolism; D012331:RNA, Fungal / Q000032:analysis; D013237:Stereoisomerism; D014158:Transcription, Genetic / Q000187:drug effects
chemical_list: C474391:10,16-dihydroxyhexadecanoic acid; D008563:Membrane Lipids; D010169:Palmitic Acids; D012331:RNA, Fungal; C000521:cutin; D011494:Protein Kinases; D002265:Carboxylic Ester Hydrolases; C019952:cutinase