- Non-stereospecific formation of 3α,7α,24-trihydroxy-5β-cholestan-26- oic acid during chenodeoxycholic acid biosynthesis
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Incubation of 3α,7α-dihydroxy-5β-cholestan-26-oic acid and its Δ24- analog with rat liver homogenate produced a mixture of C-24,25 diastereoisomers of 3α,7α,24-trihydroxy-5β-cholestan-26-oic acid, a key intermediate of chenodeoxycholic acid biosynthesis.
- Kobayashi,Hagiwara,Morisaki,Yuri,Fujimoto
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Read Online
- Engineering Regioselectivity of a P450 Monooxygenase Enables the Synthesis of Ursodeoxycholic Acid via 7β-Hydroxylation of Lithocholic Acid
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We engineered the cytochrome P450 monooxygenase CYP107D1 (OleP) from Streptomyces antibioticus for the stereo- and regioselective 7β-hydroxylation of lithocholic acid (LCA) to yield ursodeoxycholic acid (UDCA). OleP was previously shown to hydroxylate testosterone at the 7β-position but LCA is exclusively hydroxylated at the 6β-position, forming murideoxycholic acid (MDCA). Structural and 3DM analysis, and molecular docking were used to identify amino acid residues F84, S240, and V291 as specificity-determining residues. Alanine scanning identified S240A as a UDCA-producing variant. A synthetic “small but smart” library based on these positions was screened using a colorimetric assay for UDCA. We identified a nearly perfectly regio- and stereoselective triple mutant (F84Q/S240A/V291G) that produces 10-fold higher levels of UDCA than the S240A variant. This biocatalyst opens up new possibilities for the environmentally friendly synthesis of UDCA from the biological waste product LCA.
- Grobe, Sascha,Badenhorst, Christoffel P. S.,Bayer, Thomas,Hamnevik, Emil,Wu, Shuke,Grathwol, Christoph W.,Link, Andreas,Koban, Sven,Brundiek, Henrike,Gro?johann, Beatrice,Bornscheuer, Uwe T.
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p. 753 - 757
(2020/12/01)
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- Preparation method and application of seal cholic acid
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The invention provides a method for selectively separating seal cholic acid from a duck bile extract, which facilitates the utilization of the seal cholic acid which is an important biological resource in the duck bile. The invention also provides a method for preparing chenodeoxycholic acid from the seal cholic acid. Therefore, the problem of insufficient supply of chenodeoxycholic acid raw materials can be alleviated, improved. and meanwhile, corresponding biological waste pollution is also avoided. The method is easy for industrial production and has very good economic value and applicationprospect.
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- Method for preparing chenodeoxycholic acid from seal cholic acid
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The invention provides a method for preparing chenodeoxycholic acid CDCA by taking seal cholic acid as a raw material, on one hand, an application is found for seal cholic acid, and on the other hand,a new raw material source is provided for chenodeoxycholic acid, so that the problem of supply shortage of chenodeoxycholic acid crude drugs can be partially relieved, meanwhile, the problem of corresponding biological waste pollution is avoided, the problem of industrial production is well solved, and the method has very good economic value and application prospect.
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Paragraph 0039; 0049-0053; 0063-0066
(2021/02/10)
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- Synthetic method of chenodeoxycholic acid
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The invention belongs to the field of organic synthesis, and provides a synthesis method of chenodeoxycholic acid, which comprises the following steps: by using seal cholic acid which is one of the main components in the waste after chenodeoxycholic acid is extracted from duck gall paste as a raw material, carrying out methyl esterification, reacting with p-toluenesulfonyl chloride, carrying out bromine substitution, debromination, deprotection and the like to obtain chenodeoxycholic acid. The method for preparing chenodeoxycholic acid is simple, the raw material source is rich, the product yield is high, and industrialization is easy to realize.
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- Decarbonated cholesteric aldehyde as well as preparation method and application thereof
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The invention provides decarbonated cholesteric aldehyde as well as a preparation method and application thereof. The decarbonated cholesteric aldehyde is a compound as shown in a formula (I), or a salt thereof, or a stereoisomer thereof. R1 and R2 are respectively and independently selected from hydrogen, C1-C6 alkyl, halogen, hydroxyl, carboxyl, aldehyde group, amino or nitro. The decarbonated cholesteric aldehyde has good antibacterial activity, especially has a good inhibition effect on clostridium difficile, and can be used for preparing drugs for inhibiting clostridium difficile. Meanwhile, carbon-loss chenodeoxycholic acid, carbon-loss cholesteric alcohol and chenodeoxycholic acid can be prepared by taking the carbon-loss cholesteric aldehyde as an initial raw material, and the yield is high and is superior to that in the prior art. Besides, the invention provides a preparation method of various decarbonated cholesteric aldehyde, the preparation method is high in yield and purity, the raw material duck cholic acid used in the preparation method is wide in source and low in cost, an industrial method for utilizing industrial waste duck cholic acid is developed, and the industrialization of the preparation method is more feasible.
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Paragraph 0135-0137
(2021/07/21)
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- Method for synthesizing 3alpha, 7alpha-dihydroxy-5-beta-cholanic acid from duck cholic acid
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The invention belongs to the field of organic synthesis of carbocyclic compounds, and particularly relates to a method for synthesizing 3alpha, 7alpha-dihydroxy-5-beta-cholanic acid from duck cholic acid. According to the method, chenodeoxycholic acid with purity of 97.6% is synthesized by using duck cholic acid as a raw material. The comprehensive yield is 87.8%, the purity of the product is highwhile a high-temperature reaction is avoided, and later impurity removal is simple and convenient.
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Paragraph 0013
(2021/02/06)
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- Preparation method of chenodeoxycholic acid
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The invention belongs to the field of organic synthesis, and provides a preparation method of chenodeoxycholic acid, which comprises the following steps of: extracting chenodeoxycholic acid serving as one of main components in waste after chenodeoxycholic acid is extracted from duck gall paste, namely seal cholic acid, serving as a raw material; and the chenodeoxycholic acid is obtained by a propylidene protection method, acetylation, propylidene removal, methyl esterification, reaction with p-toluenesulfonyl chloride, bromine substitution, debromination, deprotection and the like. The method for preparing chenodeoxycholic acid is simple, the raw material source is rich, the product yield is high, and industrialization is easy to realize.
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Paragraph 0037; 0061-0063
(2021/05/01)
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- Preparation method of chenodeoxycholic acid
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The invention relates to the technical field of medicine synthesis, in particular to a preparation method of chenodeoxycholic acid. The invention develops a method for synthesizing the chenodeoxycholic acid by taking hyodeoxycholic acid(3alpha, 6alpha-dihydroxy-5beta-cholanic acid)as a raw material through nine steps of reaction, the reaction conditions of each step are mild, the control is easy,the process is simple, the used raw materials are wide in source, low in price and easy to obtain, the yield is high, the total yield can reach 61%, the synthesis cost is low, and the method is suitable for mass preparation and industrial production.
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Paragraph 0089-0090; 0138-0143; 0181-0183
(2021/01/24)
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- Oxidation of Primary Alcohols and Aldehydes to Carboxylic Acids via Hydrogen Atom Transfer
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The oxidation of primary alcohols and aldehydes to the corresponding carboxylic acids is a fundamental reaction in organic synthesis. In this paper, we report a new chemoselective process for the oxidation of primary alcohols and aldehydes. This metal-free reaction features a new oxidant, an easy to handle procedure, high isolated yields, and good to excellent functional group tolerance even in the presence of vulnerable secondary alcohols and tert-butanesulfinamides.
- Tan, Wen-Yun,Lu, Yi,Zhao, Jing-Feng,Chen, Wen,Zhang, Hongbin
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supporting information
p. 6648 - 6653
(2021/09/08)
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- METHOD FOR PREPARING BILE ACID DERIVATIVE BY USING CONTINUOUS FLOW REACTION
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Provided herein is a method of preparing a bile acid derivative using a continuous flow reaction. When bile acid derivatives are synthesized using a continuous flow reaction according to the present invention, the reaction is very safe compared to an existing batch-type reaction, the reaction time is significantly reduced, and high-quality bile acid derivatives may be synthesized with high efficiency. In particularly, according to the present invention, a hydrogenation reaction proceeds under substantially water-free reaction conditions, and thus the conversion rate (UDCA:CDCA) of a UDCA hydrogenation reaction may be significantly enhanced.
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Paragraph 0070-0082
(2020/09/22)
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- A method of synthesis of ursodesoxycholic acid(UDCA) using bile salt hydrolase(BSH) from Porcine intestinal flora Bifidobacterium thermophilum
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The present invention relates to a method for synthesizing ursodesoxycholic acid (UDCA) from porcine bile acid by using bile salt hydrolase (BSH) derived from Bifidobacterium thermophilum in porcine gut microbiota. The present inventors have found that, compared to existing synthesis methods involving repeated purification processes, an UDCA synthesis method using the BSH of Bifidobacterium thermophilum in porcine gut microbiota is simple and time-saving; provides remarkable advantages in terms of high-throughput production and stability; is significantly more economical; and can increase an UDCA yield. In addition, the present invention is expected to provide a significant economic advantage in that it provides high-value added UDCA effective in improving hepatic functions, alleviating fatigue through liver improvement, cholesterol reduction, gallstone dissolution, primary biliary cirrhosis, and the like by utilizing porcine waste by-products.(AA) First step : Extract bile acid derived from by-products(BB) Second step : Extract BSH enzyme(CC) Third step : Extract CDCA(DD) Fourth step : Synthesize and purify UDCA(EE) Fifth step : Analyze UDCA(FF) Process of extracting bile acid for use in UDCA synthesis in by-products, Extract bile acid soluble by use of organic solvent methanol and evaporate methanol to obtain bile acid(GG) Extract BSH enzyme by expression and purification of BSH from lactic acid bacteria having BSH enzyme used in CDCA extraction(HH) Extract bile acid from CDCA as a measure to increase the purity and yield of UDCA from extracted bile acid(II) Synthesize UDCA by redox reaction using CDCA from the bile acid extracted from respective by-products(JJ) Analyze CLA via HPLC in order to confirm the synthesis and yield of synthesized UDCACOPYRIGHT KIPO 2020
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Paragraph 0045-0046
(2020/07/11)
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- Efficient synthesis of cholic acid derivates through stereoselective C–H functionalization from hyodeoxycholic acid
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Five cholic acid derivatives (including allo-ω-muricholic acid and CDCA) were synthesized from hyodeoxycholic acid via selective oxidation of C3- or C6-hydroxyl groups by IBX and NBS oxidants and stereocontrolled conversion. The hydroxyl group could be introduced through hydrolyzing α-Br keto with K2CO3 aqueous solution or through oxidizing the double bond by monoperoxyphthalic acid. The reduction of C6-O6 carbonyl to methylene could undergo with PTSH, NaBH3CN and ZnCl2 only at 5β configuration. A feasible synthetic route of CDCA from HDCA has been established to avoid the epimerization with the yield of 45% (8 steps). These strategies provided good yields, stereoselectivity and reproducibility for the preparation of cholic acid derivates and CDCA.
- Liang, Yu-Yan,Huang, Huan,Li, Yang,Du, Rong-Kai,Li, Jing,Liu, Yong-Hong,Li, Shan,Zhang, Lei
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- METHODS FOR PREPARING BILE ACIDS
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The present disclosure provides methods of preparing cholic acid, deoxycholic acid, or chenodeoxycholic acid, an ester thereof, or a pharmaceutically or cosmetically acceptable salt thereof, and novel and useful synthetic intermediates, for example, as described for methods 1, 1A, 1B, 2, 3, 3A, and 4. The method can start with a plant derived steroid as a starting material, such as dehydroepiandrosterone (DHEA) or Acetyl-dehydroepiandrosterone (Ac-DHEA). Also provided are pharmaceutical or cosmetic compositions and uses thereof, which comprise one or more of cholic acid, deoxycholic acid, or chenodeoxycholic acid, an ester thereof, or a pharmaceutically or cosmetically acceptable salt thereof, which is of high purity, for example, free of animal derived impurities.
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- Chenodeoxycholic acid and preparation method thereof
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The invention relates to the field of medicine synthesis, and in particular to chenodeoxycholic acid and a preparation method thereof. The preparation method of the chenodeoxycholic acid provided by the invention comprises the following steps of: using 3 alpha,7 alpha-dihydroxy-5 alpha-ursodeoxycholic acid as raw materials to form an intermediate compound E through chemical reaction; then, performing chemical reaction on the intermediate compound E to form the chenodeoxycholic acid. The structure formula of the intermediate compound E is shown in the description, wherein R1 is alkyl, alkenylor aromatic group; R2 is acyl. The preparation method has the advantages that extracted byproducts can be used as raw materials for fast synthesizing the chenodeoxycholic acid; each step in the process is mild in condition; the yield is high; the method is suitable for mass preparation.
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- Chenodeoxycholic acid derivatives, preparation method thereof and medical application thereof
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The invention relates to the field of medicinal chemistry, relates to chenodeoxycholic acid derivatives, a preparation method thereof and a medical application thereof, in particular to a kind of chenodeoxycholic acid derivatives with a general formula of (I), a preparation method thereof, a pharmaceutical composition comprising the compounds and medical application thereof, especially used as drugs for preventing or treating hyperlipidaemia, type II diabetes, atherosis and non-alcoholic steatohepatitis. The formula is shown in the description.
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- Lipid accumulation inhibitory activities of novel isoxazole-based chenodeoxycholic acids: Design, synthesis and preliminary mechanism study
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In continuation of our drug discovery program on hyperlipidemia, a series of novel isoxazole-chenodeoxycholic acid hybrids were designed, synthesized and evaluated for their lipid-lowering effects. Preliminary screening of all the synthesized compounds was done by using a 3T3-L1 adipocyte model, in which the most active compound 16b could significantly reduce the lipid accumulation up to 30.5% at a nontoxic concentration 10 μM. Further mechanism studies revealed that 16b blocked lipid accumulation via activating FXR-SHP signaling pathway, efficiently down-regulated the expression of key lipogenesis regulator SREBP-1c.
- Qiu, Rongmao,Luo, Guoshun,Li, Xinyu,Zheng, Fan,Li, Haolin,Zhang, Jin,You, Qidong,Xiang, Hua
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p. 2879 - 2884
(2018/07/25)
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- Chenodeoxycholic acid synthesis method
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The invention discloses a chenodeoxycholic acid synthesis method, wherein cholic acid is used as a raw material, and 7[alpha]-hydroxyl selective oxidation, side-chain carboxyl esterification, 3[alpha]-hydroxyl esterification, 12[alpha]-hydroxymethanesulfonic acid esterification, elimination, hydrolysis, reduction and other reactions are performed to prepare the chenodeoxycholic acid. According to the present invention, the chenodeoxycholic acid synthesis method has advantages of simple step, less side reaction, high yield and easily available raw materials, is suitable for industrial production, can solve the problems of high synthesis cost, low yield and the like in the prior art, and is suitable for industrial mass-production.
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- METHODS FOR PREPARATION OF BILE ACIDS AND DERIVATIVES THEREOF
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The present application relates to a method of preparing compounds of Formula (I) or a pharmaceutically acceptable salt, solvate, or amino acid conjugate thereof, R1 is H, α-OH, β-ΟΗ, or an oxo group.
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- METHODS FOR PREPARATION OF BILE ACIDS AND DERIVATIVES THEREOF
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The present application relates to a method of preparing compounds of Formula (A) or a pharmaceutically acceptable salt, solvate, or amino acid conjugate thereof.
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- PROCESS FOR PREPARING HIGH PURITY URSODEOXYCHOLIC ACID
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The present invention describes a process for the synthesis of ursodeoxycholic acid wherein the purification of the crude ursodeoxycholic acid (containing approximately 13-15% of chenodeoxycholic acid impurity) takes place first passing through a salification with imidazole and a subsequent purification via "methyl ester", which allows a finished product with an extremely low content of known "cheno and "litho" impurities to be obtained. The present invention also describes the recovery steps of cholic acid and 3α-hydroxy-7-ketocholanic acid from the mother liquors of process intermediates.
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- Hydroxylation of lithocholic acid by selected actinobacteria and filamentous fungi
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Selected actinobacteria and filamentous fungi of different taxonomy were screened for the ability to carry out regio- and stereospecific hydroxylation of lithocholic acid (LCA) at position 7β. The production of ursodeoxycholic acid (UDCA) was for the first time shown for the fungal strains of Bipolaris, Gibberella, Cunninghamella and Curvularia, as well as for isolated actinobacterial strains of Pseudonocardia, Saccharothrix, Amycolatopsis, Lentzea, Saccharopolyspora and Nocardia genera. Along with UDCA, chenodeoxycholic (CDCA), deoxycholic (DCA), cholic (CA), 7-ketodeoxycholic and 3-ketodeoxycholic acids were detected amongst the metabolites by some strains. A strain of Gibberella zeae VKM F-2600 expressed high level of 7β-hydroxylating activity towards LCA. Under optimized conditions, the yield of UDCA reached 90% at 1 g/L of LCA and up to 60% at a 8-fold increased substrate loading. The accumulation of the major by-product, 3-keto UDCA, was limited by using selected biotransformation media.
- Kollerov,Monti,Deshcherevskaya,Lobastova,Ferrandi,Larovere,Gulevskaya,Riva,Donova
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p. 370 - 378
(2013/03/28)
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- CO2 incubator ozone sterilization device
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PROBLEM TO BE SOLVED: To provide an apparatus that ensures sterilization of a COincubator, has no leakage of fed ozone gas to the outside, uniformly circulates ozone in a storage and constantly and continuously controls an ozone concentration.SOLUTION: The apparatus for ozone sterilization of a COincubator includes: a sterilization tent 1 with an airtight hole 8a for airtightly protruding a leading end part of a tube connection part 14a provided in the COincubator 11 to the outside and a discharge part 9a for discharging ozone gas to the outside, for covering the COincubator 11 airtightly; an ozone gas generator 18 for applying circulating sterilization to the inside and the outside of the COincubator 11 covered by the sterilization tent 1 by pressure-feeding the ozone gas to the tube connection part 14a; and an ozone gas neutralization unit 26 for neutralizing and eliminating the ozone gas discharged from the discharge part 9a.
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- PROCESS FOR PRODUCTION OF STEROIDS
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It is an object of the present invention to provide a novel method for producing a steroid compound. The present invention provides a method for producing 5β-3,7-dioxocholanic acid or an ester derivative thereof, using, as a raw material, a sterol having double bonds at position 5 and at position 24, such as cholesta-5,7,24-trien-3β-ol, ergosta-5,7,24(28)-trien-3β-ol, desmosterol, fucosterol, or ergosta-5,24(28)-dien-3β-ol, via the following 4 steps: (I) a step involving oxidation of a hydroxyl group at position 3 and isomerization of a double bond at position 5 to position 4; (II) a step involving the oxidative cleavage of a side chain to convert position 24 to a carboxyl group or an ester derivative thereof; (III) a step of introducing an oxygen functional group into position 7; and (IV) a step of constructing a 5β configuration by reductive saturation of a double bond at position 4.
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Page/Page column 64
(2008/12/04)
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- PROCESS FOR THE PREPARATION OF CHOLANIC ACIDS
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A process for the preparation of high purity cholanic acids, typically in purity equal to or higher than 99%.
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Page/Page column 2
(2008/06/13)
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- A process for the preparation of cholanic acids
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A process for the preparation of high purity cholanic acids, typically in purity equal to or higher than 99%.
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Page/Page column 3
(2010/11/30)
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- 7α- and 12α-Hydroxysteroid dehydrogenases from Acinetobacter calcoaceticus lwoffii: a new integrated chemo-enzymatic route to ursodeoxycholic acid
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We report the very efficient biotransformation of cholic acid to 7-keto- and 7,12-diketocholic acids with Acinetobacter calcoaceticus lwoffii. The enzymes responsible of the biotransformation (i.e. 7α- and 12α-hydroxysteroid dehydrogenases) are partially purified and employed in a new chemo-enzymatic synthesis of ursodeoxycholic acid starting from cholic acid. The first step is the 12α-HSDH-mediated total oxidation of sodium cholate followed by the Wolf-Kishner reduction of the carbonyl group to chenodeoxycholic acid. This acid is then quantitatively oxidized with 7α-HSDH to 7-ketochenodeoxycholic acid, that was chemically reduced to ursodeoxycholic acid (70% overall yield).
- Giovannini, Pier Paolo,Grandini, Alessandro,Perrone, Daniela,Pedrini, Paola,Fantin, Giancarlo,Fogagnolo, Marco
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experimental part
p. 1385 - 1390
(2009/04/06)
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- PURIFICATION PROCESS FOR CHENODEOXYCHOLIC ACID
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The present invention relates to a process for purifying chenodeoxycholic acid (3α,7α-dihydroxy-5β-cholic acid). In particular, the present invention relates to a process for purifying chenodeoxycholic acid from low grade of chenodeoxycholic acid mixture in swine bile solid, with high yield and purity.
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Page/Page column 16
(2008/06/13)
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- Xanthomonas maltophilia CBS 897.97 as a source of new 7β- and 7α-hydroxysteroid dehydrogenases and cholylglycine hydrolase: Improved biotransformations of bile acids
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The paper reports the partial purification and characterization of the 7β- and 7α-hydroxysteroid dehydrogenases (HSDH) and cholylglycine hydrolase (CGH), isolated from Xanthomonas maltophilia CBS 897.97. The activity of 7β-HSDH and 7α-HSDH in the reduction of the 7-keto bile acids is determined. The affinity of 7β-HSDH for bile acids is confirmed by the reduction, on analytical scale, to the corresponding 7β-OH derivatives. A crude mixture of 7α- and 7β-HSDH, in soluble or immobilized form, is employed in the synthesis, on preparative scale, of ursocholic and ursodeoxycholic acids starting from the corresponding 7α-derivatives. On the other hand, a partially purified 7β-HSDH in a double enzyme system, where the couple formate/formate dehydrogenase allows the cofactor recycle, affords 6α-fluoro-3α, 7β-dihydroxy-5β-cholan-24-oic acid (6-FUDCA) by reduction of the corresponding 7-keto derivative. This compound is not obtainable by microbiological route. The efficient and mild hydrolysis of glycinates and taurinates of bile acids with CGH is also reported. Very promising results are also obtained with bile acid containing raw materials.
- Pedrini, Paola,Andreotti, Elisa,Guerrini, Alessandra,Dean, Mariangela,Fantin, Giancarlo,Giovannini, Pier Paolo
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p. 189 - 198
(2007/10/03)
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- Synthetic receptors, libraries and uses thereof
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The invention is directed to synthetic receptor(s) which comprises a polyfunctional organic template covalently linked to two or more oligomers which may independently be the same or different and may independently be straight chain or branched. The template may be linked to an identifier which uniquely defines the synthetic receptor. The identifier is a stable chemical molecule or a plurality of stable chemical molecules distinguishable and detectable to picomolar levels or may be an oligonucleotide. In an preferred embodiment, the template is covalently linked to a solid support which is linked to an identifier.
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- Fluorescent Sensors for Molecules Guest-Responsive Monomer and Excimer Fluorescence of 6A,6B-; 6A,6C-; 6A,6D-; and 6A,6E-Bis(2-naphthylsulfonyl)-γ-cyclodextrins
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Flexible hosts, 6A,6B-; 6A,6C-; 6A,6D-; and 6A,6E-bis(2-naphthylsulfonyl)-γ-cyclodextrins (γ-1, γ-2, γ-3, and γ-4, respectively) were used as fluorescent sensors with which a variety of organic compounds were detected by naphthalene excimer and monomer emissions. In a 10 vol% ethylene glycol aqueous solution, γ-1 exhibits almost pure monomer fluorescence while γ-2, γ-3, and γ-4 exhibit both monomer and excimer emissions. The intensities of the emissions changed upon addition of guest species, particularly in the case of γ-2 and γ-3, and the guest-induced intensity variations were used as sensitivity factors of the sensors. When (-)-borneol (5), cyclohexanol (6), cyclododecanol (7), and 1-adamantanecarboxylic acid (8) were added to each host solution, γ-2, γ-3, and γ-4 increased the excimer emission intensity but decreased the monomer one, the absolute intensity variations being 6 5≈8 1. When geraniol (9), nerol (10), and (-)-menthol (11) were added, the hosts decreased intensities in both monomer and excimer emissions for 9 and 10 while their emission variations for 11 were similar to those of 5. For steroids such as cholic acid (12), deoxycholic acid (13), chenodeoxycholic acid (14), and ursodeoxycholic acid (15), γ-4 showed depression in the excimer emission and enhancement in the monomer one while γ-2 and γ-3 showed complicated features in which the excimer emission was enhanced with the order of 15 14 13≈12 but the monomer one was depressed or enhanced depending on the hosts. All these data demonstrate that the hosts can be used as sensors for molecular recognition.
- Hamada, Fumio,Minato, Shingo,Osa, Tetsuo,Ueno, Akihiko
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p. 1339 - 1346
(2007/10/03)
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- Selective C-12 Oxidation of Cholic Acid
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Cholic acid amide has been regioselectively oxidized with an equivalent amount of bromine in alkaline methanol to the corresponding 12-oxo derivative (3), presumably via neighbouring N-bromo-amide group participation of an intermediate (2′).
- Miljkovic, Dusan,Kuhajda, Ksenija,Hranisavljevic, Jovan
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p. 106 - 107
(2007/10/03)
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- Process for production of chenodeoxycholic acid and novel intermediates useful for the process
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Novel intermediates useful in the synthesis of chenodeoxycholic acid, the intermediates being of the formula: STR1 wherein --X is an electron withdrawing group, n is an integer equal to zero or one, and --Y is a halogen. A process for producing such novel intermediates from 5β-cholanic acid-3α, 7α, 12α-triol methyl ester is carried out without using highly toxic and carcinogenic compounds such as dichromates and chromium trioxide.
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- Substrate Specificity of Glycyrrhizinic Acid Hydrolase
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Glycyrrhizinic acid hydrolase produced by Aspergillus niger selectively hydrolyzed the 3-O-β-D-glucuronide linkage of glycyrrhizinic acid.The substrate specificity of this enzyme was investigated for synthetic glucuronides of aliphatic alcohols as well as natural glucuronide saponins.It was revealed that the glucuronide linkage with low molecular weight alcohols was not cleaved by this enzyme, while the 3-O-β-D-glucuronide linkage saponins of oleanolic acid was selectively hydrolyzed.It was also disclosed that both the 4-hydroxyl and carboxyl groups of the glucuronide moiety must be unsubstituted for hydrolysis by this enzyme.
- Sasaki, Yasuhiro,Morita, Toshinobu,Kuramoto, Takashi,Mizutani, Kenji,Ikeda, Ryuko,Tanaka, Osamu
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p. 207 - 210
(2007/10/02)
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- Stereoselective Introduction of Steroid Side Chains. Synthesis of Chenodeoxycholic Acid
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A new short route to chenodeoxycholic acid has been developed.The synthesis is based on the stereoselective introduction of the steroidal side chain via an ene reaction of methyl acrylate and a (17Z)-ethylidene steroid prepared from androstenedione.
- Wovkulich, Peter M.,Batcho, Andrew D.,Uskokovic, Milan R.
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p. 612 - 615
(2007/10/02)
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- STEREOCHEMISTRY OF REDUCTION OF CYCLIC KETONES BY ALKALI METALS AND BY SODIUM DITHIONITE.
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An opposite stereoselectivity is observed in the reduction of 3α-hydroxy-5β-7-oxo-cholanic acid by alkali metals and by sodium dithionite, contrary to the results reported with other cyclic or bicyclic ketones.An electron-transfer mechanism followed by coupling of the ketyl radical with SO2(1-). is suggested for the reduction by sodium dithionite.
- Castaldi, Graziano,Perdoncin, Giulio,Giordano, Claudio
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p. 2487 - 2490
(2007/10/02)
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- Potential Bile Acid Metabolites. 6. Stereoisomeric 3,7-Dihydroxy-5β-cholanic Acids
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New synthetic routes to the four possible 3,7-dihydroxy acids are described.The principal reactions involved were inversions with DMF and Me2SO-crown ether and reduction of 12-oxo tosylhydrazones.Inversion of 3α-tosylates by the Me2SO-crown ether method succeeded but that of the corresponding mesylates did not.A table of 1H NMR chemical shift reference data of monosubstituted methyl cholanates pertinent to bile acid characterization has been expanded.
- Iida, Takashi,Chang, Frederic C.
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p. 2966 - 2972
(2007/10/02)
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- Process and intermediates for the synthesis of Vitamin D3 metabolites and chenodeoxycholic acid
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The present disclosure is directed to a process for the synthesis of chenodeoxychloic acid, 25-hydroxycholesterol and 1α,25-dihydroxycholesterol from 17-keto steroids. A cholic acid side chain is stereospecifically introduced by reaction of the appropriate 17-keto steroid with ethyltriphenylphosphonium halides to produce the 17-ethylidene derivative which is allowed to react with acrylic acid esters or propiolic acid esters followed by hydrogenation.
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- Process for chenodeoxycholic acid and intermediates therefore
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A multi-step synthesis of chenodeoxycholic acid from 3-keto-bisnorcholenol, a compound readily obtained from the abundant plant sterol β-sitosterol, is described. A key step in the synthesis is the stereoselective microbial introduction of the 7-alpha hydroxy group into 3-keto-bisnorcholenol.
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- Chenodeoxycholic acid recovery process
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A method of isolating chenodeoxycholic acid from hog bile is provided, which comprises the steps of treating the hog bile under saponifying conditions separating the bile acids from the water-soluble constituents of the saponified bile; esterifying the bile acids to obtain a mixture of bile acid esters; isolating from the mixture of bile acid esters the hyodeoxycholic acid ester as its adduct with a compound selected from the group consisting of benzene and toluene; treating the remaining bile acid esters under acetylating conditions; isolating the hyocholic acid ester triacetate; isolating the chenodeoxycholic acid ester diacetate; treating the chenodeoxycholic acid ester diacetate under saponifying conditions; isolating the chenodeoxycholic acid thus obtained; and, optionally purifying the chenodeoxycholic acid. The method described yields chenodeoxycholic acid of exceedingly high purity, which may be used in the treatment of gallstones by their dissolution in vivo.
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- High purity chenodeoxycholic acid and method for obtaining same
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Chenodeoxycholic acid melting in the range of 168°-171° C. and of such high purity as to be suitable for human therapeutic use is obtained by crystallization from acetonitrile.
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- Process for the purification of crude chenodeoxycholic acid
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Crude chenodeoxycholic acid is purified by subjecting an aqueous solution of an alkali salt thereof to continuous liquid-liquid extraction with a water-immiscible organic solvent until substantially all extractable impurities have been extracted. Crystalline pure free acid is obtained therefrom by acidification of the aqueous solution, extracting the free acid with organic solvent and thereafter removing the solvent, the last portion thereof preferably in the presence of water.
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- Introducing Δ11 unsaturation into steroid compounds
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A process for the introduction of Δ11 unsaturation into steroid compounds having a C-12 sulfonate ester group is described. Dehydrosulfonation is carried out by reacting the sulfonate with a hexaalkylphosphoric triamide. The process is particularly useful with steroid compounds that also contain a blocked C-7 hydroxy group. The process yields the 11-enate in preference to the 6,11-dienate. The yield of the process can be increased by carrying out the reaction in the presence of a weak base.
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