221911-67-7

Upstream product

• 371-27-7 2,2,2-trifluoroethylbutyrate 
• 698-87-3 3-phenyl-2-propanol 
• 123-20-6 vinyl n-butyrate 

Relevant academic research and scientific papers

Dual enzymatic dynamic kinetic resolution by Thermoanaerobacter ethanolicus secondary alcohol dehydrogenase and Candida antarctica lipase B

The immobilization of Thermoanaerobacter ethanolicus secondary alcohol dehydrogenase (TeSADH) using sol-gel method enables its use to racemize enantiopure alcohols in organic media. Here, we report the racemization of enantiopure phenyl-ring-containing secondary alcohols using xerogel-immobilized W110A TeSADH in hexane rather than the aqueous medium required by the enzyme. We further showed that this racemization approach in organic solvent was compatible with Candida antarctica lipase B (CALB)-catalyzed kinetic resolution. This compatibility, therefore, allowed a dual enzymatic dynamic kinetic resolution of racemic alcohols using CALB-catalyzed kinetic resolution and W110A TeSADH-catalyzed racemization of phenyl-ring-containing alcohols.

Functional expression of Serratia marcescens H30 lipase in Escherichia coli for efficient kinetic resolution of racemic alcohols in organic solvents

A lipase from Serratia marcescens H30 was cloned and functionally expressed in E. coli in soluble form (more than 80%). The recombinant lipase activity reached 25,000 U/L after optimization. Different carriers were used to immobilize the recombinant S. marcescens lipase (SmL), and LH-EP was found to be the most ideal carrier. LH-EP immobilized SmL could catalyze enantioselective resolution of racemic alcohols. Using 4-phenyl-2-butanol as the model alcohol, the effects of temperature, organic solvent, water activity, acyl donor and substrate molar ratio on the LH-EP immobilized SmL catalyzed kinetic resolution were investigated. All of these factors influenced the resolution effect to some extent. At last, a high E value of more than 200 was achieved, with ee S > 99% and a conversion of 49.9%. Further studies showed that the LH-EP immobilized SmL could also catalyze the kinetic resolution of other structure similar racemic alcohols. These results indicate that the SmL is useful for biocatalytic production of chiral alcohols. This work is the first attempt of using SmL in this field, and it further broadens the application field of SmL.

METHOD OF PREPARATION OF OPTICALLY ACTIVE ALCOHOLS

The present invention relates to a method for preparing chiral alcohol having optical activity. More specifically, the present invention relates to a method for preparing (S)-chiral alcohol with a high yield and a high optical purity by mixing achiral substrates such as racemic alcohol or ketone with metal catalyst and protein hydrolase to perform a dynamic kinetic resolution reaction.

(S)-selective dynamic kinetic resolution of secondary alcohols by the combination of subtilisin and an aminocyclopentadienylruthenium complex as the catalysts

A new procedure for the dynamic kinetic resolution (DKR) of racemic alcohols into single enantiomers is described. This procedure employs surfactant-treated subtilisin as an (S)-selective resolving catalyst and an aminocyclopentadienylruthenium complex as a racemizing catalyst. The DKR is performed best in the presence of an acyl donor such as trifluoroethyl butyrate in THF at room temperature. Eight simple secondary alcohols have been efficiently resolved with high optical purities and good yields. The subtilisin-based DKR is complementary in stereoselectivity to its lipase-based counterpart. For an acyl-carrying alcohol, both subtilisin- and lipase-based DKRs have proceeded equally well to give a pair of enantiomeric products (>99.5% ee each) with opposite optical rotations in high yields (94-95%). Copyright

Activity enhancement of pig liver esterase in organic solvents by colyophilization with methoxypolyethylene glycol: Kinetic resolution of alcohols

Colyophilization of pig liver esterase with methoxypolyethylene glycol gave a catalyst, PLE/MPEG, which showed an enhanced activity in organic solvents. The PLE/MPEG catalyzed transesterification of the alcohols rac-1a- d with vinyl propionate in toluene proceeded with good to high selectivities. The addition of up to 1% of water to the reaction mixture resulted in a significant increase in enantioselectivity. Immobilization of PLE/MPEG for the batch-wise resolution was accomplished by its spontaneous adsorption on an ultrafiltration membrane.

Enzyme reactions in apolar solvents. The resolution of branched and unbranched 2-alkanols by porcine pancreatic lipase

Straight-chain and branched 2-alkanols were subjected to enzyme catalyzed transesterification in organic solvent using porcine pancreatic lipase, high enantioselectivity being generally observed. The method was applied to the synthesis of (R)-(-)-9-hydroxy-(E)-decenoic acid, a component of the queen bee mandibular gland pheromone.