Microbial Resolution of 1-Phenoxy-2-propanol by Stereospecific Decomposition and Asymmetric Hydrolysis of 1-Phenoxy-2-propyl Acetate

Yanase, Hideshi; Arishima, Tamio; Kita, Keiko; Nagai, Jun; Mizuno, Sumiko; Takuma, Yuki; Endo, Kyoko; Kato, Nobuo

doi:10.1271/bbb.57.1334

Cited by 8 publications

(8 citation statements)

References 1 publication

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“…However, it showed a relatively low activity for an ester having a phenoxy group in an alcohol moiety, such as 1-phenoxy-2-propyl acetate, which was easily hydrolyzed with various lipases. 47,48) This again confirmed that EstAC is specific for the aromatic acid moiety. A preliminary experiment on the enantioselectivity of the enzyme indicated that EstAC preferentially hydrolyzed the (R)-and (S)-enantiomers of ethyl 2-(4-isobutylphenyl)propionate and ethyl 3-phenylbutanoate respectively.…”

Section: Substrate Specificitysupporting

confidence: 58%

A Novel Alkaline Esterase fromSporosarcinasp. nov. Strain eSP04 Catalyzing the Hydrolysis of a Wide Variety of Aryl-carboxylic Acid Esters

Takehara

Kinoshita

Miyamoto

et al. 2012

Bioscience, Biotechnology, and Biochemistry

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A novel esterase showing activity specific for esters of aryl-carboxylic acids was discovered in Sporosarcina sp. nov., which was identified by the 16S rDNA sequencing method in addition to morphological and physiological analyses. The aryl-carboxylesterase (named EstAC) was purified 780-fold from crude cell extracts by a 5-step procedure. EstAC was characterized as a monomeric protein with a molecular weight of 43,000, an optimum pH of around 9.0, and an optimum temperature of 40 C. The pH optimum and the effects of inhibitors together with an internal amino acid sequence suggested that EstAC is a member of family VIII esterases. EstAC was found to be highly active on a wide variety of substrates such as alkyl benzoates, alkyl phenylacetates, ethyl -or -substituted phenylpropionates, dialkyl terephthalates, dimethyl isophthalate, and ethylene glycol dibenzoate. However, monomethyl terephthalate was not hydrolyzed. It was suggested that EstAC had 4-hydroxybenzoyl and cinnamoyl esterase activities as well.

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Section: Substrate Specificitysupporting

confidence: 58%

A Novel Alkaline Esterase fromSporosarcinasp. nov. Strain eSP04 Catalyzing the Hydrolysis of a Wide Variety of Aryl-carboxylic Acid Esters

Takehara

Kinoshita

Miyamoto

et al. 2012

Bioscience, Biotechnology, and Biochemistry

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“…2,3) Since the strict substrate specificities of enzymes is a distinct advantage for chiral pool synthesis, microbial enzymes are often used to obtain optically pure substances. The stereospecific hydrolysis of racemic esters by esterase is an efficient strategy for optical resolution, 4) but the maximum yield of the targeted optically pure compound is below 50%. In contrast, there are two reported methods of lipase-based asymmetric synthesis of 2-substituted-1,3-propanediol monoacetate that give high yields (more than 50%).…”

mentioning

confidence: 99%

Site-Specific and Asymmetric Hydrolysis of Prochiral 2-Phenyl-1,3-propanediol Diacetate by a Bacterial Esterase from an Isolated Strain

Mitsui

Shinya

Ichiyama

et al. 2007

Bioscience, Biotechnology, and Biochemistry

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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.

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“…Kinetic optical resolution with enzymes has received considerable attention because of the high enantioselectivities than can be obtained. [13][14][15][16][17][18][19][20][21] Thus, a selection of enzymes was screened in order to identify those which were capable of catalyzing the enantioselective hydrolysis of rac-1, however in all cases no hydrolysis was observed. It is known that enzymatic hydrolysis of sterically hindered esters can be problematic, 22,23) and this suggested that the A 1,2 -strain between the ethoxycarbonyl group and sulfamoyl group of rac-1 was preventing hydrolysis.…”

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confidence: 99%

Optically Active Cyclohexene Derivative as a New Antisepsis Agent: An Efficient Synthesis of Ethyl (6R)-6-[N-(2-Chloro-4-fluorophenyl)sulfamoyl]cyclohex-1-ene-1-carboxylate (TAK-242)

Yamada

Ichikawa

Yamano

et al. 2006

CHEMICAL & PHARMACEUTICAL BULLETIN

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Sepsis and septic shock remain the chief causes of death in intensive care units, with mortality rates between 30 and 70%.1-3) Although several drug candidates have entered clinical trials over the last 20 years, most have not demonstrated significant benefit for patients with sepsis and septic shock, and difficulties of the development of an antisepsis agent has been proven. In 2001, Drotrecogin-a (Xigris TM ), 4) a recombinant human activated protein C, was launched onto the market as the first antisepsis agent, but the usefulness of this drug is limited due to its efficacy and safety.Recently, we reported that ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl)sulfamoyl]cyclohex-1-ene-1-carboxylate [TAK-242: (R)-1] was selected as a new class of clinical candidate for sepsis.5) TAK-242 exhibited potent inhibitory activity for the production of not only nitric oxide (NO) but also various cytokines such as tumor necrosis factor-alfa (TNF-a), interleukin-1-beta (IL-1b) and IL-6 in vitro, as well as potent protective effects in the mouse endotoxin shock model. (R)-1 is currently undergoing clinical trails and is expected to be a promising antisepsis drug.As shown in Chart 1, (R)-1 was obtained in high enantiomeric purity by the optical resolution of rac-1, prepared from commercially available ethyl 2-oxocyclohexane-1-carboxylate (2) in three steps, by means of preparative high performance liquid chromatography (HPLC) using a chiral stationary phase. 5) Although separation using preparative HPLC is a straightforward method for the preparation of small quantities of optically active compounds, applications to large scale production are sometimes troublesome. Thus, an efficient and practical process for the preparation of optically active (R)-1 was required in order to supply sufficient quantities for further evaluation of this compound. In this paper, we describe the development of two new synthetic methods of (R)-1 utilizing rac-1 as the synthetic precursor.In order to find an alternative synthesis of optically active (R)-1 from the rac-1, the following two routes were proposed (Chart 2): the formation and separation of diastereomeric ester derivatives I followed by the conversion to ethyl ester (Route A), and enzymatic hydrolysis of the ester derivative (if necessary, followed by ethyl esterification, Route B).The synthetic method via the preparation of diastereomeric phenethyl ester derivatives was initially investigated as shown in Chart 3. First, the synthesis of key intermediate carboxylic acid 3 by hydrolysis of rac-1 was examined using standard hydrolytic conditions employing bases such as sodium hydroxide (NaOH), lithium hydroxide, potassium carbonate (K 2 CO 3 ) and cesium carbonate (Cs 2 CO 3 ) or Lewis acids and Brønsted acids. However, in all cases hydrolysis was accompanied by significant decomposition resulting in low yields of 3. In further studies, the use of barium dihydroxide [Ba(OH) 2 ] was found to give 3 in good yield. Thus, the treatment of rac-1 with aqueous Ba(OH) 2 solution at 60°C in acetonitrile (...

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Microbial Resolution of 1-Phenoxy-2-propanol by Stereospecific Decomposition and Asymmetric Hydrolysis of 1-Phenoxy-2-propyl Acetate

Cited by 8 publications

References 1 publication

A Novel Alkaline Esterase fromSporosarcinasp. nov. Strain eSP04 Catalyzing the Hydrolysis of a Wide Variety of Aryl-carboxylic Acid Esters

A Novel Alkaline Esterase fromSporosarcinasp. nov. Strain eSP04 Catalyzing the Hydrolysis of a Wide Variety of Aryl-carboxylic Acid Esters

Site-Specific and Asymmetric Hydrolysis of Prochiral 2-Phenyl-1,3-propanediol Diacetate by a Bacterial Esterase from an Isolated Strain

Optically Active Cyclohexene Derivative as a New Antisepsis Agent: An Efficient Synthesis of Ethyl (6R)-6-[N-(2-Chloro-4-fluorophenyl)sulfamoyl]cyclohex-1-ene-1-carboxylate (TAK-242)

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