107797-26-2Relevant articles and documents
Enantiomeric specificity in a pheromone-kairomone system of two threatened saproxylic beetles, Osmoderma eremita and Elater ferrugineus
Svensson, Glenn P.,Larsson, Mattias C.
, p. 189 - 197 (2008)
The scarab beetle Osmoderma eremita and its larval predator, the click beetle Elater ferrugineus, are threatened saproxylic beetles regarded as indicators of the species-richness of insect fauna of hollow deciduous trees. Male O. eremita produce the pheromone (R)-(+)-γ-decalactone to attract conspecific females, and this compound is also utilized by E. ferrugineus as a kairomone, presumably for detection of tree hollows containing prey. We have investigated enantiomeric specificity to γ-decalactone in this pheromone-kairomone system by electrophysiological and field trapping experiments. In single-sensillum recordings from male and female O. eremita, which used the (R)-enantiomer and the racemic mixture of γ-decalactone as odor stimuli, numerous olfactory receptor neurons (ORNs) responding to both stimuli were found. No neurons responded preferentially to the racemic mixture, showing that these beetles seem to lack receptors specific for the (S)-enantiomer. The enantiomeric specificity of ORNs was confirmed by gas chromatography-linked single-sensillum recordings where the two enantiomers in a racemic mixture were separated on a chiral column. Furthermore, in field experiments that used the (R)-enantiomer and the racemic mixture as lures, the attraction of O. eremita females corresponded to the amount of (R)-enantiomer released from lures with the (S)-enantiomer displaying no antagonistic effects. Trap catch data also suggested that the (S)-enantiomer is not a behavioral antagonist for E. ferrugineus. The odor-based system can be highly efficient in attracting the larval predator where trap catch in 1 yr almost equaled the total number of specimens collected in Sweden until 1993. Our study shows that racemic γ-decalactone could be used for cost-effective monitoring of both beetles.
Short synthetic route to the enantiomerically pure (R)-(+)-γ-decalactone
Kula, Jozef,Sikora, Magdalena,Sadowska, Halina,Piwowarski, Jacek
, p. 11321 - 11324 (1996)
An efficient procedure for the preparation of homochiral (R)-(+)-γ-decalactone 4 based on castor oil ozonolysis is described. The key intermediate, (R)-(-)-1,3-nonandiol 1, was transformed into monotosylate 2 and then reacted with sodium cyanide to give (
Convenient enantioselective synthesis of new 1,4-sulfanylalcohols from γ-lactones
Filippi, Jean-Jacques,Fernandez, Xavier,Lizzani-Cuvelier, Louisette,Loiseau, André-Michel
, p. 6267 - 6270 (2002)
A synthetic strategy based upon three basic reactions - enzymatic resolution, oxygen-sulfur exchange, reduction - allowed us to carry out an easy and useful synthesis of a series of new 1,4-sulfanylalcohols from aliphatic γ-lactones. Final products have been obtained in good yields with enantiomeric excesses in a 66-91% range.
Stereoselective synthesis of chiral δ-lactonesviaan engineered carbonyl reductase
Wang, Tao,Zhang, Xiao-Yan,Zheng, Yu-Cong,Bai, Yun-Peng
, p. 10584 - 10587 (2021/10/19)
A carbonyl reductase variant,SmCRM5, fromSerratia marcescenswas obtained through structure-guided directed evolution. The variant showed improved specific activity (U mg?1) towards most of the 16 tested substrates and gave high stereoselectivities of up to 99% in the asymmetric synthesis of 13 γ-/δ-lactones. In particular, SmCRM5showed a 13.8-fold higher specific activity towards the model substrate,i.e., 5-oxodecanoic acid, and gave (R)-δ-decalactone in 99% ee with a space-time yield (STY) of 301 g L?1d?1. The preparative synthesis of six δ-lactones in high yields and with high enantiopurities showed the feasibility of the biocatalytic synthesis of these high-value-added chemicals, providing a cost-effective and green alternative to noble-metal catalysis.
A synthetic method of chiral gamma-decalactone
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Paragraph 0030-0034; 0038; 0044; 0050; 0056, (2017/10/05)
A synthetic method of chiral gamma-decalactone is provided. The method includes steps of (1) adding concentrated sulfuric acid into an organic solvent, then adding a catalyst, a ligand and a phase-transfer catalyst into the mixture, finally adding methyl 4-carbonyldecanoate into the mixture, and reacting the mixture; (2) transferring a reaction product obtained in the step (1) into an autoclave, and filling the autoclave with hydrogen to pressurize the autoclave to 3-6 MPa, with the reaction temperature being 60-120 DEG C and reaction time being 4-8 h; and (3) subjecting a reaction product obtained in the step (2) to neutralization, filtration, solvent recovery and distillation to obtain the chiral gamma-decalactone. The reaction temperature and pressure of the method are proper, and production operation is easy so that the method can be used for industrial production. The ee value of the product can be 95% or above.
Chemo-enzymatic synthesis of optically active γ- and δ-decalactones and their effect on aphid probing, feeding and settling behavior
Boratyński, Filip,Dancewicz, Katarzyna,Paprocka, Marlena,Gabrys?, Beata,Wawrzeńczyk, Czes?aw
, (2016/01/16)
The enantiomerically enriched γ- and δ-decalactones (4a and 4b) were prepared from corresponding racemic primary-secondary 1,4- and 1,5-diols (1a and 1b), as products of enzymatic oxidation catalyzed by different alcohol dehydrogenases. The results of biotransformations indicated that the oxidation processes catalyzed by alcohol dehydrogenase (HLADH), both isolated from horse liver and recombinant in Escherichia coli, were characterized by the highest degree of conversion with moderate enantioselectivity of the reaction. Useful, environmentally friendly extraction procedure of decalactones (4a and 4b) based on hydrodistillation using a Deryng apparatus was developed. Both racemic lactones (4a and 4b), as well as their enantiomerically enriched isomers, were tested for feeding deterrent activity against Myzus persicae. The effect of these compounds on probing, feeding and settling behavior of M. persicae was studied in vivo. The deterrent activity of decalactones (4a and 4b) against aphids depended on the size of the lactone ring and the enantiomeric purity of the compounds. δ-Decalactone (4b) appeared inactive againstM. persicae while γ-decalactone (4a) restrained aphid probing at ingestional phase. Only (-)-(S)-γ-decalactone (4a) had strong and durable (i.e. lasting for at least 24 hours) limiting effect, expressed at phloem level.
