Category: 90866-33-4

Category: benzofurans. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: (R)-Ethyl 4-chloro-3-hydroxybutanoate, is researched, Molecular C6H11ClO3, CAS is 90866-33-4, about Asymmetric reduction of a variety of ketones with a recombinant carbonyl reductase: identification of the gene encoding a versatile biocatalyst. Author is Ema, Tadashi; Yagasaki, Hideo; Okita, Nobuyasu; Nishikawa, Kumiko; Korenaga, Toshinobu; Sakai, Takashi.

The gene encoding a versatile biocatalyst that shows high enantioselectivity for a variety of ketones, SCR (Saccharomyces cerevisiae carbonyl reductase), has been identified, cloned, and expressed in E. coli. Recombinant E. coli co-producing SCR and GDH (glucose dehydrogenase) is an easy-to-use, synthetically useful biocatalyst, and 8 out of the 16 alcs. obtained had enantiomeric purities of >98% ee.

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Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Pellegata, R.; Dosi, I.; Villa, M.; Lesma, G.; Palmisano, G. published the article 《(-)-β-Pinene as chiral promoter. 2. Stereospecific access to (-)-γ-amino-β(R)-hydroxybutyric acid (GABOB) and (R)-carnitine》. Keywords: carnitine; aminohydroxybutyric acid; pinene chiral promoter; GABOB; stereoselective preparation carnitine.They researched the compound: (R)-Ethyl 4-chloro-3-hydroxybutanoate( cas:90866-33-4 ).COA of Formula: C6H11ClO3. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:90866-33-4) here.

Treating (-)-β-pinene (I) with RCHO (R = Cl3C, EtO2C) and FeCl3 gave 60-75% the ene adducts II. A stereochem. correlation between II and their products of alk. hydrolysis is reported. Starting from II (R = Cl3C), by using a degradative sequence, a stereocontrolled approach to (R)-γ-amino-β-hydroxybutyric acid and (R)-carnitine-HCl is described.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: (R)-Ethyl 4-chloro-3-hydroxybutanoate(SMILESS: O=C(OCC)C[C@@H](O)CCl,cas:90866-33-4) is researched.Related Products of 1762-34-1. The article 《Chiral alcohol production by NADH-dependent phenylacetaldehyde reductase coupled with in situ regeneration of NADH》 in relation to this compound, is published in European Journal of Biochemistry. Let’s take a look at the latest research on this compound (cas:90866-33-4).

Phenylacetaldehyde reductase (PAR) produced by styrene-assimilating Corynebacterium strain ST-10 was used to synthesize chiral alcs. This enzyme with a broad substrate range reduced various prochiral aromatic ketones and β-ketoesters to yield optically active secondary alcs. with an enantiomeric purity of more than 98% enantiomeric excess (e.e.). The Escherichia coli recombinant cells which expressed the par gene could efficiently produce important pharmaceutical intermediates; (R)-2-chloro-1-(3-chlorophenyl)ethanol (28 mg·mL-1) from m-chlorophenacyl chloride, Et (R)-4-chloro-(3-hydroxy butanoate) (28 mg·mL-1) from Et 4-chloro-3-oxobutanoate and (S)-N-tert-butoxycarbonyl(Boc)-3-pyrrolidinol from N-Boc-3-pyrrolidinone (51 mg·mL-1), with more than 86% yields. The high yields were due to the fact that PAR could concomitantly reproduce NADH in the presence of 3-7% (volume/volume) 2-propanol in the reaction mixture This biocatalytic process provided one of the best asym. reductions ever reported.

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Benzofuran – Wikipedia,
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The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: (R)-Ethyl 4-chloro-3-hydroxybutanoate( cas:90866-33-4 ) is researched.Synthetic Route of C6H11ClO3.Jung, Jihye; Park, Hyun Joo; Uhm, Ki-Nam; Kim, Dooil; Kim, Hyung-Kwoun published the article 《Asymmetric synthesis of (S)-ethyl-4-chloro-3-hydroxy butanoate using a Saccharomyces cerevisiae reductase: Enantioselectivity and enzyme-substrate docking studies》 about this compound( cas:90866-33-4 ) in Biochimica et Biophysica Acta, Proteins and Proteomics. Keywords: ethylchlorohydroxy butanoate Saccharomyces reductase enantioselectivity. Let’s learn more about this compound (cas:90866-33-4).

Et (S)-4-chloro-3-hydroxy butanoate (ECHB) is a building block for the synthesis of hypercholesterolemia drugs. In this study, various microbial reductases have been cloned and expressed in Escherichia coli. Their reductase activities toward ethyl-4-chloro oxobutanoate (ECOB) have been assayed. Amidst them, Baker’s yeast YDL124W, YOR120W, and YOL151W reductases showed high activities. YDL124W produced (S)-ECHB exclusively, whereas YOR120W and YOL151W made (R)-form alc. The homol. models and docking models with ECOB and NADPH elucidated their substrate specificities and enantioselectivities. A glucose dehydrogenase-coupling reaction was used as NADPH recycling system to perform continuously the reduction reaction. Recombinant E. coli cell co-expressing YDL124W and Bacillus subtilis glucose dehydrogenase produced (S)-ECHB exclusively.

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Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Tetrahedron Letters called A practical asymmetric synthesis of carnitine, Author is Kitamura, M.; Ohkuma, T.; Takaya, H.; Noyori, R., which mentions a compound: 90866-33-4, SMILESS is O=C(OCC)C[C@@H](O)CCl, Molecular C6H11ClO3, Name: (R)-Ethyl 4-chloro-3-hydroxybutanoate.

The asym. hydrogenation of ClCH2COCH2CO2Et (I) catalyzed by Ru(OAc)2[(S)-binap] [binap = 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl] gave 97% (R)-ClCH2CH(OH)CH2CO2Et [(R)-II] with 97% enantiomeric excess. (R)-II can be converted to (R)-carnitine (III) by standard methods. The asym. hydrogenation of I catalyzed by Ru(OAc)2[(R)-binap] gave (S)-II.

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Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Article, Research Support, Non-U.S. Gov’t, Journal of Biotechnology called Effective biosynthesis of ethyl (R)-4-chloro-3-hydroxybutanoate by supplementation of L-glutamine, D-xylose and β-cyclodextrin in n-butyl acetate-water media, Author is He, Yu-Cai; Tao, Zhi-Cheng; Ding, Yun; Zhang, Dan-Ping; Wu, Yin-Qin; Lu, Yun; Liu, Feng; Xue, Yu-Feng; Wang, Cheng; Xu, Jian-He, which mentions a compound: 90866-33-4, SMILESS is O=C(OCC)C[C@@H](O)CCl, Molecular C6H11ClO3, Application of 90866-33-4.

To avoid adding NAD+ and effectively transform Et 4-chloro-3-oxobutanoate, the mixture of L-glutamine (200 mM) and D-xylose (250 mM) was added into in Bu acetate-water (10:90, volume/volume) biphasic system instead of NAD+ for increasing the biocatalytic efficiency. To further improve the synthesis of optically pure Et (R)-4-chloro-3-hydroxybutanoate (>99% ee), β-cyclodextrin was also added into this reaction media, and Et (R)-4-chloro-3-hydroxybutanoate (>99% ee) could be effectively synthesized from 800 mM Et 4-chloro-3-oxobutanoate in the yield of 100% by whole-cells of recombinant Escherichia coli CCZU-A13. Finally, the possible mechanism for improving the reductase activity by supplementation of L-glutamine, D-xylose and β-CD was proposed. In conclusion, this strategy has high potential for the effective biosynthesis of Et (R)-4-chloro-3-hydroxybutanoate (>99% ee).

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Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: (R)-Ethyl 4-chloro-3-hydroxybutanoate, is researched, Molecular C6H11ClO3, CAS is 90866-33-4, about Purification and characterization of a novel carbonyl reductase with high stereo-selectivity.Recommanded Product: 90866-33-4.

A novel NADPH dependent carbonyl reductase was separated from Candida parapsilosis CCTCC 203011. The enzyme gave a single band on SDS-PAGE, which was purified through ammonium sulfate, DEAE Sepharose FF, Phenyl-Sepharose FF and Blue Sepharose FF chromatog. from cell-free extract The mol. mass of the enzyme was about 30 kD. The optimum pH and temperature for reduction were 4.5 and 35°C, resp. The Cu2+ had strong restrictive effect on enzyme activity. In addition, the carbonyl reductase was an enzyme with high substrate specificity and stereo-selectivity, and showed high asym. reduction activity toward α-hydroxyacetophenone and Et 4-chloroacetoacetate. For the asym. reduction of α-hydroxyacetophenone and Et 4-chloroacetoacetate, (S)-1-phenyl-1,2-ethanediol and (R)-Et 4-chloro-3-hydroxybutanoate were produced by the purified enzyme, with the 100% and 94.3% e.e value, resp. So the enzyme could be one of the effective biocatalysts for asym. synthesis of chiral alcs. The amino acid sequences of one peptide from the purified enzyme were analyzed by LC-MASS-MASS, and the carbonyl reductase showed some identity to the hypothetical protein CaO19.10414 reported.

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The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: (R)-Ethyl 4-chloro-3-hydroxybutanoate(SMILESS: O=C(OCC)C[C@@H](O)CCl,cas:90866-33-4) is researched.Safety of Tri-n-octylphosphine Oxide. The article 《Yeast catalyzed reduction of β-keto esters (1): Factors affecting whole-cell catalytic activity and stereoselectivity》 in relation to this compound, is published in Biocatalysis and Biotransformation. Let’s take a look at the latest research on this compound (cas:90866-33-4).

Six yeasts were studied for their ability to reduce Et 4-chloroacetoacetate (Et 4-chloro-3-oxobutanoate) stereoselectively. Five species reduced the substrate to Et (S)-4-chloro-3-hydroxybutanoate of high (92-99%) optical purity. With glucose-grown cells, substrate reduction could only be demonstrated when growth was oxygen-limited, whereas xylose-grown Pichia capsulata could be grown under conditions of oxygen excess without losing its reducing ability. Zygosaccharomyces rouxii exhibited high enantioselectivity (≥98% ee (S)-enantiomer) under all conditions tested, while in P. capsulata, a novel switch was observed from producing mainly the (S)-enantiomer using glucose as co-substrate to producing mainly the (R)-enantiomer using 2-propanol as co-substrate. This switch was correlated with a change in reduction predominantly from an NADPH-dependent dehydrogenase system to an NADH-dependent system. In the production of Et (R)-4-chloro-3-hydroxybutanoate with P. capsulata, the enantioselectivity was also found to depend upon growth conditions. With glucose-grown cells, higher enantioselectivity was observed using cells harvested in stationary phase (93-94% ee) compared with cells harvested in exponential phase (43-60% ee). Growing P. capsulata with xylose rather than glucose as the major source of carbon for growth resulted in an eight-fold increase in the specific rate of Et (R)-4-chloro-3-hydroxybutanoate production using 2-propanol as co-substrate, although enantioselectivity was slightly reduced (65-81% ee) compared with the maximum achieved with glucose-grown cells. The effect of growth on xylose could also be correlated with enhanced activity of an NADH-dependent (R)-selective dehydrogenase system.

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Benzofuran – Wikipedia,
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In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called Microbial asymmetric reduction of ethyl 4-chloro-3-oxobutanoate to optically active ethyl 4-chloro-3-hydroxybutanoate, published in 1990-08-31, which mentions a compound: 90866-33-4, Name is (R)-Ethyl 4-chloro-3-hydroxybutanoate, Molecular C6H11ClO3, Recommanded Product: 90866-33-4.

The synthesis of Et (R)-4-chloro-3-hydroxybutanoate through the asym. reduction of Et 4-chloro-3-oxobutanoate with the NADPH-dependent aldehyde reductase of Sporobolomyces salmonicolor AKU 4429 is described. Under preparative scale reaction conditions with the acetone-fractionated aldehyde reductase, the amount of Et 4-chloro-3-hydroxybutanoate reached 33.2 mg/mL (molar yield, 74.0%). Furthermore, conversion to Et (S)-4-chloro-3-hydroxybutanoate occurred on incubation with washed cells of Trichosporon cutaneum AKU 4864 as the catalyst.

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Benzofuran – Wikipedia,
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The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: (R)-Ethyl 4-chloro-3-hydroxybutanoate(SMILESS: O=C(OCC)C[C@@H](O)CCl,cas:90866-33-4) is researched.Recommanded Product: 4774-24-7. The article 《Synthesis of ethyl (S)-4-chloro-3-hydroxybutanoate using fabG-homologues》 in relation to this compound, is published in Applied Microbiology and Biotechnology. Let’s take a look at the latest research on this compound (cas:90866-33-4).

This paper is a report on the successful application of bioinformatics to enzyme screening. The synthesis of Et (S)-4-chloro-3-hydroxybutanoate (ECHB) by asym. reduction of Et 4-chloroacetoacetate (ECAA) using fabG-homolog was studied. β-Ketoacyl-acyl carrier protein reductases from both Escherichia coli and Bacillus subtilis, which are components of type II fatty acid synthase, could reduce ECAA to (S)-ECHB with 94-98% ee. Furthermore, acetoacetyl-CoA reductases (ARs) from both Ralstonia eutropha and Zoogloea ramigera, whose genes are significantly similar to fabG genes and play a physiol. role in the biosynthesis of poly-β-3-hydroxybutyrate, could also catalyze the asym. reduction of ECAA to (S)-ECHB with >99% ee. (S)-ECHB was synthesized to 48.7 g/l with an optical purity of 99.8% ee, using recombinant E. coli cells coexpressing AR from R. eutropha and glucose dehydrogenase from B. subtilis for the regeneration of NADPH.

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Benzofuran – Wikipedia,
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