107797-27-3Relevant articles and documents
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 0062; 0065-0069, (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.
Simple Preparation of Rhodococcus erythropolis DSM 44534 as Biocatalyst to Oxidize Diols into the Optically Active Lactones
Martinez-Rojas, Enriqueta,Olejniczak, Teresa,Neumann, Konrad,Garbe, Leif-Alexander,Boraty?ski, Filip
, p. 623 - 627 (2016/10/11)
In the current study, we present a green toolbox to produce ecological compounds like lactone moiety. Rhodococcus erythropolis DSM 44534 cells have been used to oxidize both decane-1,4-diol (2a) and decane-1,5-diol (3a) into the corresponding γ- (2b) and δ-decalactones (3b) with yield of 80% and enantiomeric excess (ee)?=?75% and ee?=?90%, respectively. Among oxidation of meso diols, (?)-(1S,5R)-cis-3-oxabicyclo[4.3.0]non-7-en-2-one (5a) with 56% yield and ee?=?76% as well as (?)-(2R,3S)-cis-endo-3-oxabicyclo[2.2.1]dec-7-en-2-one (6a) with 100% yield and ee?=?90% were formed. It is worth mentioning that R. erythropolis DSM 44534 grew in a mineral medium containing ethanol as the sole source of energy and carbon Chirality 28:623–627, 2016.
