About: Total Synthesis, Proof of Absolute Configuration, and Biosynthetic Origin of Stylopsal, the First Isolated Sex Pheromone of Strepsiptera

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About: Total Synthesis, Proof of Absolute Configuration, and Biosynthetic Origin of Stylopsal, the First Isolated Sex Pheromone of Strepsiptera Goto Sponge NotDistinct Permalink

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
Description	The asymmetric total synthesis of the diastereomers of stylopsal establishes the absolute configuration of the first reported sex pheromone of the twisted-wing parasite Stylops muelleri as (3R,5R,9R)-trimethyldodecanal. The key steps for the diastereo- and enantiodivergent introduction of the methyl groups are two different types of asymmetric conjugate addition reactions of organocopper reagents to alpha,beta-unsaturated esters, whereas the dodecanal skeleton is assembled by Wittig reactions. The structure of the natural product was confirmed by chiral gas chromatography (GC) techniques, GC/MS and GC/electroantennography (EAD) as well as field tests. An investigation into the biosynthesis of the pheromone revealed that it is likely to be produced by decarboxylation of a 4,6,10-trimethyltridecanoic acid derivative, which was found in substantial amounts in the fat body of the female, but not in the host bee Andrena vaga. This triple-branched fatty acid precursor thus seems to be biosynthesized de nov The asymmetric total synthesis of the diastereomers of stylopsal establishes the absolute configuration of the first reported sex pheromone of the twisted-wing parasite Stylops muelleri as (3R,5R,9R)-trimethyldodecanal. The key steps for the diastereo- and enantiodivergent introduction of the methyl groups are two different types of asymmetric conjugate addition reactions of organocopper reagents to alpha,beta-unsaturated esters, whereas the dodecanal skeleton is assembled by Wittig reactions. The structure of the natural product was confirmed by chiral gas chromatography (GC) techniques, GC/MS and GC/electroantennography (EAD) as well as field tests. An investigation into the biosynthesis of the pheromone revealed that it is likely to be produced by decarboxylation of a 4,6,10-trimethyltridecanoic acid derivative, which was found in substantial amounts in the fat body of the female, but not in the host bee Andrena vaga. This triple-branched fatty acid precursor thus seems to be biosynthesized de nov (en)
Title	Total Synthesis, Proof of Absolute Configuration, and Biosynthetic Origin of Stylopsal, the First Isolated Sex Pheromone of Strepsiptera Total Synthesis, Proof of Absolute Configuration, and Biosynthetic Origin of Stylopsal, the First Isolated Sex Pheromone of Strepsiptera (en)
skos:prefLabel	Total Synthesis, Proof of Absolute Configuration, and Biosynthetic Origin of Stylopsal, the First Isolated Sex Pheromone of Strepsiptera Total Synthesis, Proof of Absolute Configuration, and Biosynthetic Origin of Stylopsal, the First Isolated Sex Pheromone of Strepsiptera (en)
skos:notation	RIV/60460709:41320/13:60377!RIV14-MSM-41320___
http://linked.open...avai/predkladatel	Fakulta lesnická a dřevařská
http://linked.open...avai/riv/aktivita	I P S
http://linked.open...avai/riv/aktivity	I, P(GAP506/10/1466), S
http://linked.open...iv/cisloPeriodika	26
http://linked.open...vai/riv/dodaniDat	2014
http://linked.open...aciTvurceVysledku	Šobotník, Jan
http://linked.open.../riv/druhVysledku	J - Článek v odborném periodiku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Česká zemědělská univerzita v Praze / Fakulta lesnická a dřevařská
http://linked.open...dnocenehoVysledku	111314
http://linked.open...ai/riv/idVysledku	RIV/60460709:41320/13:60377
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	asymmetric synthesis, configuration determination, pheromones, total synthesis, Wittig reactions (en)
http://linked.open.../riv/klicoveSlovo	Wittig reactions configuration determination total synthesis pheromones asymmetric synthesis
http://linked.open...odStatuVydavatele	CZ - Česká republika
http://linked.open...ontrolniKodProRIV	[B90F87CF977E]
http://linked.open...i/riv/nazevZdroje	CHEMISTRY-A EUROPEAN JOURNAL
http://linked.open...in/vavai/riv/obor	CC
http://linked.open...ichTvurcuVysledku	1 (xsd:int)
http://linked.open...cetTvurcuVysledku	10 (xsd:int)
http://linked.open...vavai/riv/projekt	Strepsiptera of the genus Stylops (Stylopidae): evolution of host specificity, chemical ecology and behaviour of parasitised host
http://linked.open...UplatneniVysledku	2013
http://linked.open...v/svazekPeriodika	19
http://linked.open...iv/tvurceVysledku	Cvačka, Josef Jiroš, Pavel Straka, Jakub Černá, Kateřina Šobotník, Jan Kalinová, Blanka Šebesta, Petr Jahn, Ullrich Lagoutte, Roman Jirošová, Anna
http://linked.open...ain/vavai/riv/wos	000320390500021
issn	0947-6539
number of pages	10 (xsd:int)
http://localhost/t...ganizacniJednotka	41320

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