Synthesis and Inhibitory Properties of Pheromone Analogs for the Epoxide Hydrolase of the Gypsy Moth

Graham, Steven M.; Prestwich, Glenn D.

doi:10.1021/jo00090a012

Cited by 47 publications

(19 citation statements)

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“…The latter compound is a very useful intermediate towards the fluorinated synthon 17 used, for instance in the preparation of the 13,13 difluoro HODE [17]. It can be noted that such a gem-difluorination in propargylic position was also a key step in the preparation of the fluoro analogues of the disparlure pheromone [19]. Therefore this propargylic route is again a key issue with regard to the preparation of the desired gem-difluoro allylic compounds.…”

Section: Gem-difluorination Studiesmentioning

confidence: 99%

The propargylic route as efficient entry to monofluoro and gem-difluoro compounds: mechanistic considerations

Prakesch

Kerouredan

Grée

et al. 2004

Journal of Fluorine Chemistry

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Section: Gem-difluorination Studiesmentioning

confidence: 99%

The propargylic route as efficient entry to monofluoro and gem-difluoro compounds: mechanistic considerations

Prakesch

Kerouredan

Grée

et al. 2004

Journal of Fluorine Chemistry

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“…In contrast, enzymatic resolution of epoxide becomes increasingly attractive [2,6,36]. Epoxide hydrolases (EHs, EC 3.3.2.3), which are used to catalyze the hydrolysis of epoxides to the corresponding vicinal trans-diols [4,5,19,25,33], are ubiquitous in nature and occur in many organisms, including mammals [35], insects [21], plants [12] and microorganisms [3,18,26,32,38]. Recent studies on EH production from Aspergillus niger are exciting due to its highly enantioselective nature [1,3,22,29].…”

Section: Introductionmentioning

confidence: 99%

Enzymatic resolution of racemic phenyloxirane by a novel epoxide hydrolase from Aspergillus niger SQ-6 and its fed-batch fermentation

Liu

Qian

et al. 2005

J IND MICROBIOL BIOTECHNOL

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A microorganism with the ability to catalyze the resolution of racemic phenyloxirane was isolated and identified as Aspergillus niger SQ-6. Chiral capillary electrophoresis was successfully applied to separate both phenyloxirane and phenylethanediol. The epoxide hydrolase (EH) involved in this resolution process was (R)-stereospecific and constitutively expressed. When whole cells were used during the biotransformation process, the optimum temperature and pH for stereospecific vicinal diol production were 35 degrees C and 7.0, respectively. After a 24-h conversion, the enantiomer excess of (R)-phenylethanediol produced was found to be >99%, with a conversion rate of 56%. In fed-batch fermentations at 30 degrees C for 44 h, glycerol (20 g L(-1)) and corn steep liquor (CSL) (30 g L(-1)) were chosen as the best initial carbon and nitrogen sources, and EH production was markedly improved by pulsed feeding of sucrose (2 g L(-1) h(-1)) and continuous feeding of CSL (1 g L(-1) h(-1)) at a fermentation time of 28 h. After optimization, the maximum dry cell weight achieved was 24.5+/-0.8 g L(-1); maximum EH production was 351.2+/-13.1 U L(-1) with a specific activity of 14.3+/-0.5 U g(-1). Partially purified EH exhibited a temperature optimum at 37 degrees C and pH optimum at 7.5 in 0.1 M phosphate buffer. This study presents the first evidence for the existence of a predicted epoxide racemase, which might be important in the synthesis of epoxide intermediates.

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“…[5,6,8] It has been shown that substitutions in the polar group of lepidoptera pheromone molecules result in reduced recognition by the olfactory receptors [9] and produce potent inhibitors of the pheromonecatabolizing enzymes present in the olfactory tissues. [10] ated using an EAG test. The EAG activity of these point-fluorinated pheromone analogues indicates that the point of fluorination has a critical influence on the pheromone activity.…”

Section: Introductionmentioning

confidence: 99%

“…[1] An electroantennogram (EAG) investigation, [10,11] however, of these pheromone analogues 2 revealed that both the (ϩ)-2 and (Ϫ)-2 enantiomers were as active as the natural eldanolide (ϩ)-1 toward the insect olfactory receptors.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Activity of Point‐Fluorinated Pheromone Analogues of Eldana saccharina

et al. 2004

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Substitution of fluorine atoms on an organic molecule makes it possible to modify the molecular orbital and electron density of the surface without changing its molecular shape. Point‐fluorinated analogues of the sex pheromone of the male African sugarcane borer were synthesized in optically active forms and their pheromone activities were investigated using an EAG test. The EAG activity of these point‐fluorinated pheromone analogues indicates that the point of fluorination has a critical influence on the pheromone activity. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

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Synthesis and Inhibitory Properties of Pheromone Analogs for the Epoxide Hydrolase of the Gypsy Moth

Cited by 47 publications

References 0 publications

The propargylic route as efficient entry to monofluoro and gem-difluoro compounds: mechanistic considerations

The propargylic route as efficient entry to monofluoro and gem-difluoro compounds: mechanistic considerations

Enzymatic resolution of racemic phenyloxirane by a novel epoxide hydrolase from Aspergillus niger SQ-6 and its fed-batch fermentation

Synthesis and Biological Activity of Point‐Fluorinated Pheromone Analogues of Eldana saccharina

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