69765-34-0Relevant academic research and scientific papers
Convenient double-enzymatic synthesis of both enantiomers of 6-methyl-ε-caprolactone
van As, Bart A.C.,Chan, Dah-Kee,Kivit, Patrick J.J.,Palmans, Anja R.A.,Meijer
, p. 787 - 790 (2007)
Both enantiomers of 6-methyl-ε-caprolactone (6-MeCL) are obtained in high enantiomeric excess by the combination of an enzymatic ring opening of racemic 6-methyl-ε-caprolactone and subsequent enzymatic ring closure. Immobilized Candida antarctica lipase B (Novozym 435) was selected as the biocatalyst for both the ring-opening and the ring-closing reaction. This route provides ready access to enantiopure (S)-6-MeCL (ee = 99.6%) and (R)-6-MeCL (ee = 98.8%).
First chemo-enzymatic synthesis of the (R)-Taniguchi lactone and substrate profiles of CAMO and OTEMO, two new Baeyer–Villiger monooxygenases
Rudroff, Florian,Fink, Michael J.,Pydi, Ramana,Bornscheuer, Uwe T.,Mihovilovic, Marko D.
, p. 157 - 165 (2017/01/17)
Abstract: This study investigates the substrate profile of cycloalkanone monooxygenase and 2-oxo-Δ3-4,5,5-trimethylcyclopentenylacetyl-coenzyme A monooxygenase, two recently discovered enzymes of the Baeyer–Villiger monooxygenase family, used as whole-cell biocatalysts. Biooxidations of a diverse set of ketones were performed on analytical scale: desymmetrization of substituted prochiral cyclobutanones and cyclohexanones, regiodivergent oxidation of terpenones and bicyclic ketones, as well as kinetic resolution of racemic cycloketones. We demonstrated the applicability of the title enzymes in the enantioselective synthesis of (R)-(?)-Taniguchi lactone, a building block for the preparation of various natural product analogs such as ent-quinine. Graphical abstract: [Figure not available: see fulltext.]
Lipase-catalyzed doubly enantioselective ring-opening resolution between alcohols and lactones: Synthesis of chiral hydroxyl esters with two stereogenic centers
Xia, Bo,Li, Yanyan,Cheng, Guilin,Lin, Xianfu,Wu, Qi
, p. 3448 - 3454 (2015/04/16)
A novel lipase B from Candida antarctica-catalyzed doubly enantioselective ring-opening resolution between racemic alcohols and lactones was developed. By using this strategy, three optically pure compounds including hydroxyl esters with two stereogenic centers and recovered alcohols and lactones were obtained simultaneously in high yields and ee. This process was used for the resolution of various racemic alcohols with different substituent groups and lactones with different ring sizes (four- and seven- membered lactones). The scale-up experiments were also successful. Moreover, molecular docking was performed to explain the molecular basis of this doubly enantioselective ring-opening resolution. As an attractive and efficient strategy, lipase-catalyzed doubly enantioselective ring-opening resolution will be widely used in the synthesis of optically pure hydroxyl esters with two stereogenic centers. Opening new doors: A novel lipase B from Candida antarctica-catalyzed doubly enantioselective ring-opening resolution between racemic alcohols and lactones is developed.
Enzymatic Resolution of Medium-Ring Lactones. Synthesis of (S)-(+)-Phoracantholide I
Fouque, Elie,Rousseau, Gerard
, p. 661 - 666 (2007/10/02)
The horse liver and pig liver esterase hydrolysis of racemic medium ring lactones gives with excellent enantiomeric excess the S- (or R) lactones and the corresponding R- (or S) hydroxy acids.This is the first general method to obtain optically pure medium ring lactones.Application to the preparation of (S)-(+)-Phoracantholide I is reported.
