- In-situ and one-step preparation of protein film in capillary column for open tubular capillary electrochromatography enantioseparation
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In this work, the phase-transitioned BSA (PTB) film using the mild and fast fabrication process adhered to the capillary inner wall uniformly, and the fabricated PTB film-coated capillary column was applied to realize open tubular capillary electrochromatography (OT-CEC) enantioseparation. The enantioseparation ability of PTB film-coated capillary was evaluated with eight pairs of chiral analytes including drugs and neurotransmitters, all achieving good resolution and symmetrical peak shape. For three consecutive runs, the relative standard deviations (RSD) of migration time for intra-day, inter-day, and column-to-column repeatability were in the range of 0.3%–3.5%, 0.2%–4.9% and 2.1%–7.7%, respectively. Moreover, the PTB film-coated capillary column ran continuously over 300 times with high separation efficiency. Therefore, the coating method based on BSA self-assembly supramolecular film can be extended to the preparation of other proteinaceous capillary columns.
- Li, Ling,Xue, Xuqi,Zhang, Huige,Lv, Wenjuan,Qi, Shengda,Du, Hongying,Manyande, Anne,Chen, Hongli
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supporting information
p. 2139 - 2142
(2021/04/07)
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- PROCESS FOR THE SYNTHESIS OF OPTICALLY ACTIVE BETA-AMINO ALCOHOLS
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Subject-matter of the present invention is a process for the preparation of optically active phenyl-beta-amino alcohols by means of a specific reduction of the corresponding phenyl-beta-amino ketones. Further subject-matter of the invention are said novel synthesis intermediates and their use for the preparation of active pharmaceutical ingredients.
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Page/Page column 11-12
(2019/11/04)
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- Evaluation of the Edman degradation product of vancomycin bonded to core-shell particles as a new HPLC chiral stationary phase
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A modified macrocyclic glycopeptide-based chiral stationary phase (CSP), prepared via Edman degradation of vancomycin, was evaluated as a chiral selector for the first time. Its applicability was compared with other macrocyclic glycopeptide-based CSPs: TeicoShell and VancoShell. In addition, another modified macrocyclic glycopeptide-based CSP, NicoShell, was further examined. Initial evaluation was focused on the complementary behavior with these glycopeptides. A screening procedure was used based on previous work for the enantiomeric separation of 50 chiral compounds including amino acids, pesticides, stimulants, and a variety of pharmaceuticals. Fast and efficient chiral separations resulted by using superficially porous (core-shell) particle supports. Overall, the vancomycin Edman degradation product (EDP) resembled TeicoShell with high enantioselectivity for acidic compounds in the polar ionic mode. The simultaneous enantiomeric separation of 5 racemic profens using liquid chromatography-mass spectrometry with EDP was performed in approximately 3?minutes. Other highlights include simultaneous liquid chromatography separations of rac-amphetamine and rac-methamphetamine with VancoShell, rac-pseudoephedrine and rac-ephedrine with NicoShell, and rac-dichlorprop and rac-haloxyfop with TeicoShell.
- Hellinghausen, Garrett,Lopez, Diego A.,Lee, Jauh T.,Wang, Yadi,Weatherly, Choyce A.,Portillo, Abiud E.,Berthod, Alain,Armstrong, Daniel W.
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p. 1067 - 1078
(2018/08/01)
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- Preparation method of (R)-epinephrine
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The invention discloses a preparation method of (R)-epinephrine. The method comprises the following advantages: 1) a novel preparation technology of (R)-epinephrine is provided; 2) the process is simple, the reaction condition is mild, and the method has a large application prospect; and 3) the obtained product has the advantages of high optical purity and high optical yield.
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- PROCESS FOR THE PREPARATION OF OPTICALLY ENRICHED ADRENALINE
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A process for the production of (-)-adrenaline and (-)-adrenaline-L-tartrate is provided. The process provides for a new, efficient and commercially feasible process for the optical resolution of racemic adrenaline. In one aspect, a one pot process for the synthesis of (-)-adrenaline is provided. The process provides a simple and less expensive 5 process that can be used to prepare commercial scale batches of (-)-adrenaline and (-)-adrenaline-L-tartrate of API quality. The process avoids the use of expensive and unpredictable chiral catalysts.
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Paragraph 0044-0045
(2016/06/01)
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- A Method for Synthesizing a Catecholamine Using Plasma Polymerization
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The present invention relates to a method for manufacturing a catecholamine-based compound using a plasma polymerization method and, more specifically, to a method for artificially synthesizing a unimolecular compound capable of having various catecholamines, i.e. a hydroxyl group (-OH) as a ortho-group of a benzene ring and various alkylamines as a para-group, from a catecholamine precursor material such as phenol, aniline, etc, using a dry plasma polymerization method.COPYRIGHT KIPO 2015
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- Purification and characterization of a novel carbonyl reductase involved in oxidoreduction of aromatic β-amino ketones/alcohols
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Aromatic β-amino ketones/alcohols such as adrenalone play an important role in some stereoselective synthesis of pharmaceuticals. Unfortunately, the transformation of aromatic β-amino ketones to their chiral alcohols has been carried out chemically as no corresponding biocatalyst has been available. Here, a novel carbonyl reductase responsible for the reduction of adrenalone to (R)-(-)-epinephrine was identified and characterized from Kocuria rhizophila. This enzyme was purified to homogeneity by ammonium sulfate precipitation followed by ion-exchange column chromatography, hydrophobic chromatography and gel chromatography. The purified enzyme yielded pure (R)-enantiomer product with high activity and utilized NADH as the cofactor. The enzyme had special significance by showing selectivity for many aromatic β-amino ketones/alcohols such as 2-amino-acetophenone, 2-amino-4′- hydroxyacetophenone, isoproterenol and ephedrine. The maximum reaction rate (Vmax) and apparent Michaelis-Menten constant (Km) for adrenalone and NADH were 14.62 μmol/(min mg) protein and 0.189 mM, 11.66 μmol/(min mg) protein and 0.204 mM respectively. These properties ensure the enzyme a promising future for industrial application as a replacement of chemical synthesis of aromatic β-amino chiral alcohols.
- He, Shengbin,Wang, Zhenshou,Zou, Yang,Chen, Shaofang,Xu, Xiaoping
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p. 1107 - 1112
(2014/06/10)
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- PROCESSES FOR THE PREPARATION OF EPINEPHRINE
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The invention relates to efficient and cost effective processes for the preparation of pure (-)- epinephrine. More particularly, it relates to processes for the resolution of racemic epinephrine.
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Page/Page column 7
(2009/03/07)
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- Electroreductive generation of (S)-(+)-N,N-dimethyl-2-(hydroxymethyl)- pyrrolidinium mercury compound for enantioselective synthesis of 2-amino-1-alkyl/aryl ethanols
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(S)-(+)-N, N - Dimethyl-2-(hydroxymethyl)-pyrrolidinium (DMHP +)-mercury compound mediated enantioselective reduction of aminomethyl alkyl/aryl ketones in dimethylformamide-2-propanol (9:1) has been carried out using tetrabutylammonium tetrafluoroborate as a supporting electrolyte. The products viz. 2-amino-1-alkyl/aryl ethanols have been obtained in good yield (68-92%) with 35-91% optical purity and have been assigned (S)-configuration. The pinacol (racemic/meso) derivatives are also isolated as minor products (yield 5-20%) via dimerization of radical anion followed by protonation.
- Yadav, Ashok K.,Manju, Meera
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p. 2770 - 2772
(2008/04/18)
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- Scavenger assisted combinatorial process for preparing libraries of amides, carbamates and sulfonamides
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This invention relates to a novel solution phase process for the preparation of amide, carbamate, and sulfonamide combinatorial libraries. These libraries have utility for drug discovery and are used to form wellplate components of novel assay kits.
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- An in situ procedure for catalytic, enantioselective acetate aldol addition. Application to the synthesis of (R)-(-)-epinephrine
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We report an in situ preparation of catalyst 3 which substantially simplifies the experimental procedure for the enantioselective, catalytic acetate aldol addition reaction. The addition of Me3SiCl and Et3N circumvents the azeotropic removal of the released isopropanol upon treating ligands 1 and 2 with Ti(O(i)Pr)4. Importantly, this new procedure maintains the salient features of the catalytic process we originally described: high yields and enantioselectivities, low catalyst loads, and convenient reaction times and temperatures. We have applied the new procedure to an efficient synthesis of (R)-(-)-epinephrine from commercially available reagents in an overall yield of 45%.
- Singer, Robert A.,Carreira, Erick M.
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p. 927 - 930
(2007/10/03)
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- Methods and compositions for making liposomes
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Liposome-forming materials containing a long chain aliphatic or aromatic-based acid or amine, hydrating agents and discrete amounts of water form gels which are useful drug delivery systems and spontaneously form highly stable liposomes in aqueous solution having very high capture efficiency.
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- 3-methoxy-4-hydroxyphenylglycol fluorescence polarization immunoassay
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The present invention is directed to a fluoroescence polarization immunoassay for determining the 3-methoxy-4-hydroxyphenylglycol content in body fluids, to the various components needed for preparing and carrying out such an assay, and to methods of making these components. Specifically, tracers, immunogens and antibodies are disclosed, as well as methods for preparing them. The assay is conducted by measuring the degree of polarization of plane polarized light that has been passed through a sample containing antiserum and tracer.
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- Pharmaceutical formula
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The present invention concerns a pharmacological vehicle or carrier system, which makes possible administration of the active ingredient with a high absorption thereof in the blood circulation of the patient treated therewith, in particular also in the case of oral administration. The pharmacological vehicle system according to the invention comprises ultrafine particles of a reaction product of a reactive derivative of an at least dibasic inorganic acid or an alkane-carboxylic acid having 2 or 3 carboxyl groups and optionally one or two hydroxy groups, wherein one bond of the dibasic inorganic acid or one carboxy group of the alkane-carboxylic acid is bonded to a pharmacological active ingredient containing a hydroxy group, SH group and/or a primary or secondary amino group having a ractive hydrogen atom on this group, and the other bond is bonded to the free hydroxy group of a glycerolipid having at least one free hydroxy group on the glycerol. The invention further concerns these reaction products and a process for the preparation of ultrafine particles of these reaction products.
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- Stabilized aqueous catecholamine solutions
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An aqueous solution for treating glaucoma comprises 0.1-5.0% of a specially purified catecholamine e.g., epinephrine, 0.5-5.0% of a thiol, e.g., N-acetyl-L-cysteine, an acid compound unless the thiol is acid) to solubilize the catecholamine and a base e.g., NH4 OH to bring the pH to 6.0-7.5, the solution being free from borate ions. The acid compound, if used can be e.g., lactic acid, which may be buffered with ammonium lactate, or ammonium dihydrogen phosphate; preferably alkali metal ions are avoided. Guanethidine or like compounds which potentiate epinephrine can also be present.
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