140134-31-2Relevant academic research and scientific papers
Enantioselective biooxidation of racemic trans-cyclic vicinal diols: One-pot synthesis of both enantiopure (S,S)-cyclic vicinal diols and (R)-α-hydroxy ketones
Zhang, Jiandong,Xu, Tingting,Li, Zhi
supporting information, p. 3147 - 3153 (2013/12/04)
Highly regio- and enantioselective alcohol dehydrogenases BDHA (2,3-butanediol dehydrogenase from Bacillus subtilis BGSC1A1), CDDHPm (cyclic diol dehydrogenase from Pseudomonas medocina TA5), and CDDHRh (cyclic diol dehydrogenase from Rhodococcus sp. Moj-3449) were discovered for the oxidation of racemic trans-cyclic vicinal diols. Recombinant Escherichia coli expressing BDHA was engineered as an efficient whole-cell biocatalyst for the oxidation of (±)-1,2-cyclopentanediol, 1,2-cyclohexanediol, 1,2-cycloheptane-diol, and 1,2-cyclooctanediol, respectively, to give the corresponding (R)-α-hydroxy ketones in >99% ee and (S,S)-cyclic diols in >99% ee at 50% conversion in one pot. Escherichia coli (BDHA-LDH) co-expressing lactate dehydrogenase (LDH) for intracellular regeneration of NAD+ catalyzed the regio- and enantioselective oxidation of (±)-1,2-dihydroxy-1,2,3,4- tetrahydronaphthalene to produce the corresponding (R)-α-hydroxy ketone in >99% ee and (S,S)-cyclic diol in 96% ee at 49% conversion. Preparative biotransformations were also demonstrated. Thus, a novel and useful method for the one-pot synthesis of both vicinal diols and α-hydroxy ketones in high ee was developed via high Copyright
Studies of the deracemization of (±)-2-hydroxy-1-tetralone by trichosporon cutaneum
Lunardi, Ines,Cazetta, Tarcila,Conceicao, Gelson J. A.,Moran, Paulo J. S.,Rodrigues, J. Augusto R.
, p. 925 - 932 (2008/03/27)
The diastereo- and enantioselective bioreduction of (±)-2-hydroxy-1- tetralone (6) to the corresponding enantiopure (1S,2R)-cis-1,2-dihydroxy-1,2,3, 4-tetrahydronaphthalene (1) (83% isolated yield, >99% ee), mediated by resting cells of the yeast Trichosporon cutaneum CCT 1903 through dynamic kinetic resolution is reported. Deracemization of (±)-6 was observed in kinetic studies on the biotransformation of the enantiomers (R)-6 and (S)-6.
A Very Mild, Catalytic and Versatile Procedure for α-Oxidation of Ketone Silyl Enol Ethers Using (salen)Manganese(III) Complexes; A New, Chiral Complex Giving Asymmetric Induction. A Possible Model for Selective Biochemical Oxidative Reactions Through Eno
Reddy, D. Reddeppa,Thornton, Edward R.
, p. 172 - 173 (2007/10/02)
Facile, catalytic, selective (racemic and asymmetric) oxidation of ketone silyl enol ethers to give α-oxygenated products proceeds well under very mild, aprotic conditions using a racemic (salen)manganese(III) complex H2salen = bis(salicylidene)ethylened
