98409-21-3Relevant academic research and scientific papers
New and Convenient Chemoenzymatic Syntheses of (S)-2-Hydroxy-3-octanone, the Major Pheromone Component of Xylotrechus spp., and Its R-Enantiomer
Puigmartí, Marc,Bosch, María Pilar,Coll, Josep,Guerrero, Angel
, p. 1561 - 1568 (2017/03/21)
New and efficient chemoenzymatic approaches for the synthesis of both enantiomers of 2-hydroxy-3-octanone in good yields and excellent enantioselectivity are presented. The S-enantiomer is a pheromone component of economically important pests in Japan, India, China, and other Asian countries. The enzymatic approaches involve transesterification of the racemic acyloin with vinyl acetate in the presence of Candida antarctica lipase B (CAL B) in 99% ee of both enantiomers (E = 167-618), or hydrolysis of the acetylated acyloin by double kinetic resolution with CAL B and C. antarctica lipase A (CAL A) in 96-98% ee of either enantiomer (E = 458). CAL A and CAL B induce reverse enantioselectivity.
Synthesis of the deuterated sex pheromone components of the grape borer, xylotrechus pyrrhoderus
Kiyota, Ryutaro,Yamakawa, Rei,Iwabuchi, Kikuo,Hoshino, Keita,Ando, Tetsu
experimental part, p. 2252 - 2256 (2010/08/03)
Adult males of the grape borer, Xylotrechus pyrrho- derus, secrete (S)-2-hydroxy-3-octanone [(S)-1] and (2S,3S)-2,3-octanediol [(2S,3S)-2] from their nota of prothoraces as sex pheromone components. Their structural similarity suggests that one of them is the biosynthetic precursor of the other component. In order to confirm the biochemical conversion, deuterated derivatives of both components were synthesized by starting from a Wittig reaction between hexanal and an ylide derived from D5-iodoethane and ending with enantiomeric resolution by chiral HPLC. The molecular ions of 1 and 2 could scarcely be detected by using a GC- MS analysis, and the labeled compounds showed similar mass spectra to the unlabeled pheromone components. However, several fragment ions, including four deuterium atoms, were observed in the mass spectra of their acetate derivatives, indicating that the conversion could be confirmed by examining a compound with the diagnostic ions after acetylation of the volatiles collected from insects treated with the labeled precursors.
Deracemization of (±)-2,3-disubstituted oxiranes via biocatalytic hydrolysis using bacterial epoxide hydrolases: Kinetics of an enantioconvergent process
Kroutil, Wolfgang,Mischitz, Martin,Faber, Kurt
, p. 3629 - 3636 (2007/10/03)
Asymmetric biocatalytic hydrolysis of (±)-2,3-disubstituted oxiranes leading to the formation of vicinal diols in up to 97% ee at 100% conversion was accomplished by using the epoxide hydrolase activity of various bacterial strains. The mechanism of this deracemization was elucidated by 18OH2-labelling experiments using a partially purified epoxide hydrolase from Nocardia EH1. The reaction was shown to proceed in an enantioconvergent fashion by attack of OH- at the (S)-configured oxirane carbon atom with concomitant inversion of configuration. A mathematical model developed for the description of the kinetics was verified by the determination of the four relative rate constants governing the regio- and enantio-selectivity of the process.
ISOLATION AND IDENTIFICATION OF THE MALE SEX PHEROMONE OF THE GRAPE BORER XYLOTRECHUS PYRRHODERUS BATES (COLEOPTERA: CERAMBYCIDAE)
Sakai, Tsutomu,Nakagawa, Yoshiko,Takahashi, Jiro,Iwabuchi, Kikuo,Ishii, Kenji
, p. 263 - 264 (2007/10/02)
The sex pheromone of grape borer, Xylotrechus pyrrhoderus Bates, was isolated from body extracts and container washings of male insects, and was determined to be a mixture of (2S,3S)-octanediol (1) and (2S)-hydroxy-3-octanone (2).Each compound showed special response in electroantennogram experiments.The females were attracted by 80:20 to 95:5 mixtures of 1 and 2.This is the first time that the male sex pheromone from Cerambycidae species has been isolated and determined.
