51410-49-2Relevant academic research and scientific papers
Exploring the synthetic applicability of a cyanobacterium nitrilase as catalyst for nitrile hydrolysis
Mukherjee, Chandrani,Zhu, Dunming,Biehl, Edward R.,Hua, Ling
, p. 5238 - 5242 (2006)
The substrate specificity and synthetic applicability of the nitrilase from cyanobacterium Synechocystis sp. strain PCC 6803 have been examined. This nitrilase catalyzed the hydrolysis of both aromatic and aliphatic nitriles to the corresponding acids in high yields. Furthermore, the stereoselective hydrolysis of phenyl-substituted β-hydroxy nitriles to (S)-enriched β-hydroxy carboxylic acids and selective hydrolysis of α,ω- dinitriles with five or less methylene groups to ω-cyano carboxylic acids have been achieved. This suggested that nitrilase from Synechocystis sp. PCC 6803 could be a useful enzyme catalyst for the "green" nitrile hydrolysis. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
Evaluation of a new protocol for enzymatic dynamic kinetic resolution of 3-hydroxy-3-(aryl)propanoic acids
Koszelewski, Dominik,Zysk, Malgorzata,Brodzka, Anna,Zadlo, Anna,Paprocki, Daniel,Ostaszewski, Ryszard
supporting information, p. 11014 - 11020 (2015/11/24)
The application of tandem metal-enzyme dynamic kinetic resolution (DKR) is a powerful tool for the manufacture of high-value chemical commodities. A new protocol of kinetic resolution based on irreversible enzymatic esterification of carboxylic acids with orthoesters was introduced to obtain optically active β-hydroxy esters. This procedure was combined with metal catalyzed racemization of the target substrate providing both (R) and (S) enantiomers of ethyl 3-hydroxy-3-(4-nitrophenyl)propanoate with a high yield of 89% at 40°C. A substantial influence of the enzyme type, organic co-solvent, and metal catalyst on the conversion and enantioselectivity of the enzymatic dynamic kinetic resolution was noted.
Acetic acid aldol reactions in the presence of trimethylsilyl trifluoromethanesulfonate
Downey, C. Wade,Johnson, Miles W.,Lawrence, Daniel H.,Fleisher, Alan S.,Tracy, Kathryn J.
supporting information; experimental part, p. 5351 - 5354 (2010/10/20)
(Figure presented) In the presence of TMSOTf and a trialkylamine base, acetic acid undergoes aldol addition to non-enolizable aldehydes under exceptionally mild conditions. Acidic workup yields the β-hydroxy carboxylic acid. The reaction appears to procee
Oxime-Containing Acyl Guanidines as Beta-Secretase Inhibitors
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Page/Page column 13-14, (2010/11/28)
There is provided a series of substituted oxime-containing acyl guanidines of Formula (I) or a stereoisomer; or a nontoxic pharmaceutically acceptable salt thereof, wherein R1, R2, R3, R4, R5, R6
Reactivity and acid-base behavior of ring-methoxylated arylalkanoic acid radical cations and radical zwitterions in aqueous solution. Influence of structural effects and pH on the benzylic C-H deprotonation pathway
Bietti, Massimo,Capone, Alberto
, p. 5260 - 5267 (2007/10/03)
A product and time-resolved kinetic study of the one-electron oxidation of ring-methoxylated phenylpropanoic and phenylbutanoic acids (Ar(CH 2)nCO2H, n = 2, 3) has been carried out at different pH values. Oxidation leads t
Enzymatic nitrile hydrolysis catalyzed by nitrilase ZmNIT2 from maize. An unprecedented β-hydroxy functionality enhanced amide formation
Mukherjee, Chandrani,Zhu, Dunming,Biehl, Edward R.,Parmar, Rajiv R.,Hua, Ling
, p. 6150 - 6154 (2007/10/03)
To explore the synthetic potential of nitrilase ZmNIT2 from maize, the substrate specificity of this nitrilase was studied with a diverse collection of nitriles. The nitrilase ZmNIT2 showed high activity for all the tested nitriles except benzonitrile, producing both acids and amides. For the hydrolysis of aliphatic, aromatic nitriles, phenylacetonitrile derivatives and dinitriles, carboxylic acids were the major products. Unexpectedly, amides were found to be the major products in nitrilase ZmNIT2-catalyzed hydrolysis of β-hydroxy nitriles. The hydrogen bonding between the hydroxyl group and nitrogen in the enzyme-substrate complex intermediates that disfavors the loss of ammonia and formation of acyl-enzyme intermediate, which was further hydrolyzed to acid, was proposed to be responsible for the unprecedented β-hydroxy functionality assisted high yield of amide formation.
A convenient generation of acetic acid dianion
Parra, Margarita,Sotoca, Enrique,Gil, Salvador
, p. 1386 - 1388 (2007/10/03)
The lithium enediolate of acetic acid can be generated efficiently, as a 0.5 M solution in THF, using lithium amides prepared from n-butyllithium in THF and either diethylamine or 1,3,3-trimethyl-6-azabicyclo-(3.2.1)-octane (AZA). Its reaction with carbon
Indenone synthesis. Improved synthetic protocol and effect of substitution on the intramolecular Friedel-Crafts acylation
Galatsis, Paul,Manwell, Jeffrey J.,Blackwell, James M.
, p. 1656 - 1659 (2007/10/02)
An improved protocol for the construction of substituted indenones is presented. Also the effect of substitution on the intramolecular Friedel-Crafts acylation was noted. Specifically, if there is no substitution at the 2-position of the indenone poor yields of cyclized material were obtained, if at all, while the substitution of a methyl or ethyl group greatly improved the yield of cyclized material. Placement of a large group (e. g., benzyl) resulted in a diminuation of the improved yield. The new synthetic procedure could, in principle, allow for the construction of 2,3-disubstituted indenones. One example of this reaction mode was presented.
