- Expanding the repertoire of nitrilases with broad substrate specificity and high substrate tolerance for biocatalytic applications
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Enzymatic conversion of nitriles to carboxylic acids by nitrilases has gained significance in the green synthesis of several pharmaceutical precursors and fine chemicals. Although nitrilases from several sources have been characterized, there exists a scope for identifying broad spectrum nitrilases exhibiting higher substrate tolerance and better thermostability to develop industrially relevant biocatalytic processes. Through genome mining, we have identified nine novel nitrilase sequences from bacteria and evaluated their activity on a broad spectrum of 23 industrially relevant nitrile substrates. Nitrilases from Zobellia galactanivorans, Achromobacter insolitus and Cupriavidus necator were highly active on varying classes of nitriles and applied as whole cell biocatalysts in lab scale processes. Z. galactanivorans nitrilase could convert 4-cyanopyridine to achieve yields of 1.79 M isonicotinic acid within 3 h via fed-batch substrate addition. The nitrilase from A. insolitus could hydrolyze 630 mM iminodiacetonitrile at a fast rate, effecting 86 % conversion to iminodiacetic acid within 1 h. The arylaliphatic nitrilase from C. necator catalysed enantioselective hydrolysis of 740 mM mandelonitrile to (R)-mandelic acid in 4 h. Significantly high product yields suggest that these enzymes would be promising additions to the suite of nitrilases for upscale biocatalytic application.
- Rayavarapu, Pratima,Shah, Shikha,Sunder, Avinash Vellore,Wangikar, Pramod P.
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p. 289 - 296
(2020/05/18)
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- Oxidation of Alkynyl Boronates to Carboxylic Acids, Esters, and Amides
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A general efficient protocol was developed for the synthesis of carboxylic acids, esters, and amides through oxidation of alkynyl boronates, generated directly from terminal alkynes. This protocol represents the first example of C(sp)?B bond oxidation. This approach displays a broad substrate scope, including aryl and alkyl alkynes, and exhibits excellent functional group tolerance. Water, primary and secondary alcohols, and amines are suitable nucleophiles for this transformation. Notably, amino acids and peptides can be used as nucleophiles, providing an efficient method for the synthesis and modification of peptides. The practicability of this methodology was further highlighted by the preparation of pharmaceutical molecules.
- Li, Chenchen,Li, Ruoling,Zhang, Bing,Zhao, Pei,Zhao, Wanxiang
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supporting information
p. 10913 - 10917
(2020/05/25)
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- Preparation method of acid with different substituent groups
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The invention discloses a preparation method of an acid with different substituent groups. A terminal alkyne is lithiated with n-butyllithium, and then reacts with isopropoxyboronic acid pinacol ester, hydrogen chloride is added to achieve quenching, then the obtained reaction product is oxidized by an oxidizing agent, and the oxidized reaction product is separated and purified to obtain the acid.The method of the invention has the advantages of simplicity in operation, one-pot process preparation, no metal catalysis, nontoxic reagents, greenness, environmental friendliness and high atomic utilization rate, and provides a novel and quick way for preparing the acid with different substituent groups; and the obtained acid is an important fine chemical product, and can be widely used in fields of medicines, pesticides, spices and other industries.
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Paragraph 0103-0107
(2019/10/23)
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- acyl triazole derivative and its manufacturing method
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PROBLEM TO BE SOLVED: To provide a novel acyl triazole derivative that can be synthesized at low cost by a convenient method, has a comparable reactivity to an acid chloride with an amine compound and an alcohol compound, and can be safely handled, and a method of manufacturing the same; the acyl triazole derivative that is useful as a reactant applied to polymerization reaction to be continued; and a monomer comprising the same.SOLUTION: An acyl triazole derivative is shown by formula (1). In the formula, A denotes a substituted arylene group, a 1,3-phenylene group, a bisarylene group, a polycyclic arylene group, an alkylene group or an aralkylene group.
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Paragraph 0057
(2017/04/03)
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- PHENYLENE OXO-DIESTER PLASTICIZERS AND METHODS OF MAKING
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A process for making non-phthalate, 1,2-phenylene oxo-diester plasticizers for polymer compositions, by selectively hydrogenating naphthalene to form a partially hydrogenated naphthalene, oxygenating said partially hydrogenated naphthalene to form phenylene diacids, and esterifying said phenylene diacids with oxo-alcohols to form 1,2-phenylene oxo-diesters. Also a process for making phenylene oxo-diester plasticizers by selectively brominating xylenes to form bisbromomethylbenzene, catalytic carboalkoxylation of the bromo-compound to form phenylene diacetate, followed by transesterification to form the phenylene oxo-diester.
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Page/Page column 20
(2011/04/25)
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- Enzymatic desymmetrization route to ethyl [3-(2-amino-2-methylpropyl) phenyl]acetate
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An efficient process to ethyl [3-(2-amino-2-methylpropyl)phenyl]acetate 6 has been developed. Key steps include a novel enzymatic desymmetrization of diester 2 and a Ritter reaction between alcohol 4 and chloroacetonitrile, followed by chemoselective deprotection with thiourea.
- De Koning, Pieter D.,Gladwell, Iain R.,Morrison, Natalie A.,Moses, Ian B.,Panesar, Maninder S.,Pettman, Alan J.,Thomson, Nicholas M.,Yazbeck, Daniel R.
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experimental part
p. 871 - 875
(2012/06/18)
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- Quinolone derivatives
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A class of 2-(1H)-quinolone derivatives, substituted at the 3-position by an optionally substituted aryl substituent, are selective non-competitive antagonists of NMDA receptors and/or are antagonists of AMPA receptors, and are therefore of utility in the treatment of conditions, such as neurodegenerative disorders, convulsions or schizophrenia, which require the administration of an NMDA and/or AMPA receptor antagonist.
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- CARBONYLATION OF 1,4-DI(CHLOROMETHYL)BENZENE AND ALLYL CHLORIDE IN METHANOL, CATALYZED BY DICOBALT OCTACARBONYL
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The effects of inorganic base on the yield and selectivity of carbonylation of 1,4-di(chloromethyl)benzene and allyl chloride, catalyzed by dicobalt octacarbonyl, in methanol with carbon monoxide at atmospheric pressure have been examined.The highest yields of products were obtained with K2CO3 and Na2CO3.Addition of MeI results in a considerable increase in yields in the presence of calcium bases, givimg dimethyl 1,4-phenylenediacetate, which in the absence of MeI is formed in appreciable amounts only in the presence of sodium carbonate.
- Terekhova, M. I.,Kron, T. E.,Petrova, N. E.,Petrov, E. S.
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p. 2101 - 2104
(2007/10/02)
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- Synthesis and Physical Properties of First 5,5'-Bridged Bis(1,3-dithiolylium-4-olates)
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The synthesis and spectroscopic properties of the novel title compounds of type 6 and 17, which contain two identical mesoionic systems linked together at the 5-positions, as well as the polymerization to 18 and the dimerization of 6c-e to 20a-c are described.
- Gotthardt, Hans,Pflaumbaum, Wolfgang
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p. 411 - 420
(2007/10/02)
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