110230-69-8Relevant academic research and scientific papers
Site-specific and asymmetric hydrolysis of prochiral 2-phenyl-1,3- propanediol diacetate by a bacterial esterase from an isolated strain
Mitsui, Ryoji,Shinya, Seiho,Ichiyama, Yuichi,Kudo, Kenta,Tsuno, Takuo,Tanaka, Mitsuo
, p. 1858 - 1864 (2007)
Bacillus cereus 809A and Burkholderia sp. 711C were isolated from soil. These strains demonstrate hydrolysis activity towards prochiral 2-phenyl-1,3-propanediol diacetate and accumulated the corresponding chiral monoacetates into the reaction mixture. When 2-phenyl 1,3-propanediol diacetate was used as a substrate, the produced monoacetates with Burkholderia sp. 711C were obtained in a racemic form but that produced by Bacillus cereus 809A showed an excess of the (S)-form. The resting cell reaction revealed that for Bacillus cereus 809A, there was an enrichment of one of the enantiomers of the monoacetate such that the enantiomeric excess (e.e.) of the (S)-form was over 95%. The purified enzyme from Bacillus cereus 809A hydrolyzed diacetate to monoacetate, and the e.e. value of the (S)-form increased by prolonged reaction in a way similar to the resting cell reaction. From N-terminal amino acids, this esterase is conserved in some strains of Bacillus for which the genomic sequences have been reported.
Chiral phosphoric acid catalyzed highly enantioselective desymmetrization of 2-substituted and 2,2-disubstituted 1,3-diols via oxidative cleavage of benzylidene acetals
Meng, Shan-Shui,Liang, Yong,Cao, Kou-Sen,Zou, Lufeng,Lin, Xing-Bang,Yang, Hui,Houk,Zheng, Wen-Hua
, p. 12249 - 12252 (2014)
A highly enantioselective catalytic protocol for the desymmetrization of a wide variety of 2-substituted and 2,2-disubstituted 1,3-diols is reported. This reaction proceeds through the formation of an "ortho ester" intermediate via oxidation of 1,3-diol benzylidene acetal by dimethyldioxirane (DMDO) and the subsequent proton transfer catalyzed by chiral phosphoric acid (CPA). The mechanism and origins of enantioselectivity of this reaction are identified using DFT calculations. The oxidation by DMDO is rate-determining, and the phosphoric acid significantly accelerates the proton transfer; the attractive interactions between the benzylidene part of the substrate and the 2,4,6-triisopropyl group of CPA are the key to high enantioselectivity.
Acyclic phenylalkanediols as substrates for the study of enzyme recognition: Synthesis of substrates and enzymatic resolution via hydrolysis and transesterification
Rumbero, Angel,Borreguero, Isabel,Sinisterra, Jose V.,Alcantara, Andres R.
, p. 14947 - 14960 (2007/10/03)
Different racemic or prochiral phenyl alkane (1,n)-diols were synthesized, and their resolution was carried out by two different strategies: enzymatic transesterification with vinyl acetate, or enzymatic hydrolysis of their corresponding diacetates, in both cases catalysed by porcine pancreatic lipase (PPL). The absolute configuration of the optically enriched reaction products was determined by formation of Mosher's esters or by the use of the Benzene Sector and Benzene Chirality Rules as obtained from the Circular Dichroism spectra.
Chemo-enzymatic synthesis of 1,2- and 1,3- amino-alcohols and their use in the enantioselective reduction of acetophenone and anti-acetophenone oxime methyl ether with borane
Didier, Eric,Loubinoux, Bernard,Ramos Tombo, Gerardo H.,Rihs, Grety
, p. 4941 - 4958 (2007/10/02)
New chiral amino-alcohols were enantioselectively synthesized using biotransformations as the key steps. They were used as ligand in the enantioselective borane reduction of acetophenone and of the corresponding anti oxime methyl ether.
Enzyme catalyzed monohydrolysis of 2-aryl-1 3-propanediol diacetates. A study of structural effects of the aryl moiety on the enantioselectivity
Guanti, Giuseppe,Narisano, Enrica,Podgorski, Tadeusz,Thea, Sergio,Williams, Andrew
, p. 7081 - 7092 (2007/10/02)
PPL catalyzed monohydrolysis of 2-aryl substituted 13-propanediol diacetates afforded the corresponding monoacetates in acceptable to fair chemical and optical yields. Electronic effects in the aromatic ring were examined. Elaboration of some 2-arylpropanediol monoacetates to optically active 2-arylpropanols and propanoic acids was performed.
SYNTHESIS OF BOTH ENANTIOMERIC FORMS OF 2-SUBSTITUTED 1,3-PROPANEDIOL MONOACETATES STARTING FROM A COMMON PROCHIRAL PRECURSOR, USING ENZYMATIC TRANSFORMATIONS IN AQUEOUS AND IN ORGANIC MEDIA
Tombo, G. M. Ramos,Schaer, H.-P.,Busquets Fernandez I,Ghisalba, O.
, p. 5707 - 5710 (2007/10/02)
A direct entry to both enantiomeric forms c and ent-c based on enzyme catalyzed transformations of prochiral compounds of type a and b is described.The catalysts used are carboxyl esterase preparations obtained from crude porcine pancreas lipase.
