38335-22-7Relevant academic research and scientific papers
Bio-inspired enantioselective full transamination using readily available cyclodextrin
Zhang, Shiqi,Li, Guangxun,Liu, Hongxin,Wang, Yingwei,Cao, Yuan,Zhao, Gang,Tang, Zhuo
, p. 4203 - 4208 (2017/02/05)
The mimics of vitamin B6-dependent enzymes that catalyzed an enantioselective full transamination in the pure aqueous phase have been realized for the first time through the establishment of a new “pyridoxal 5′-phosphate (PLP) catalyzed non-covalent cyclodextrin (CD)-keto acid inclusion complexes” system, and various optically active amino acids have been obtained.
Synthesis, biological evaluation and molecular modeling studies of psammaplin A and its analogs as potent histone deacetylases inhibitors and cytotoxic agents
Wen, Jiachen,Bao, Yu,Niu, Qun,Liu, Jiang,Yang, Jinyu,Wang, Wanqiao,Jiang, Tao,Fan, Yinbo,Li, Kun,Wang, Jian,Zhao, Linxiang,Liu, Dan
supporting information, p. 4372 - 4376 (2016/08/18)
In this study, a concise synthetic method of psammaplin A was achieved from 3-bromo-4-hydroxybenzaldahyde and hydantoin through a four-step synthesis via Knoevenagel condensation, hydrolysis, oximation and amidation in 37% overall yield. A collection of novel psammaplin A analogs focused on the variations of substituents at the benzene ring and modifications at the oxime moiety were synthesized. Among all the synthesized compounds, 5d and 5e showed better HDAC inhibition than psammaplin A and comparable cytotoxicity against four cancer cell lines (PC-3, MCF-7, A549 and HL-60). Molecular docking and dynamics simulation revealed that (i) hydrogen atom of the oxime group interacts with Asp99 of HDAC1 through a water bridged hydrogen bond and (ii) a hydroxyl group is optimal attached on the para-position of benzene, interacting with Glu203 at the entrance to the active site tunnel.
Deracemisation of aryl substituted α-hydroxy esters using Candida parapsilosis ATCC 7330: Effect of substrate structure and mechanism
Baskar,Pandian,Priya,Chadha, Anju
, p. 12296 - 12306 (2007/10/03)
Candida parapsilosis ATCC 7330 was found to be an efficient biocatalyst for the deracemisation of aryl α-hydroxy esters (65-85% yield and 90-99% ee). A variety of aryl and aryl substituted α-hydroxy esters were synthesized to reflect steric and electronic effects on biocatalytic deracemisation. The mechanism of this biocatalytic deracemisation was found to be stereoinversion.
Synthesis and activity of novel analogs of hemiasterlin as inhibitors of tubulin polymerization: Modification of the a segment
Yamashita, Ayako,Norton, Emily B.,Kaplan, Joshua A.,Niu, Chuan,Loganzo, Frank,Hernandez, Richard,Beyer, Carl F.,Annable, Tami,Musto, Sylvia,Discafani, Carolyn,Zask, Arie,Ayral-Kaloustian, Semiramis
, p. 5317 - 5322 (2007/10/03)
Analogs of HTI-286 (1), containing various aromatic rings in the A segment, were synthesized as potential inhibitors of tubulin polymerization, and the structure-activity relationships related to stereo- and regio-chemical effects of substituents on the a
Method for preparation of arylpyruvic acid
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, (2008/06/13)
A method for the preparation of optionally substituted arylpyruvic acids by reaction of optionally substituted arylmethylhalides with carbon monoxide in the presence of a metal carbonyl compound and a base is disclosed wherein the base is an alkali metal hydroxide, the process is carried out at a temperature of -10° to +70° C. in the presence of an alcohol or cyclic ether.
Process for preparing α-keto-carboxylic acids from acyl halides
-
, (2008/06/13)
A process for the production of α-keto-carboxylic acids of the general formula: STR1 wherein R1 and R2 are the same or different and are hydrogen, hydrocarbyl radicals, substituted hydrocarbyl radicals or hydrocarbyloxy radicals by reacting an acyl halide of the formula: STR2 wherein R1 and R2 are as defined above and X represents halogen, in a liquid solvent medium, with an alkali metal tetracarbonyl cobaltate complex of the formula: wherein M is an alkali metal to form the corresponding acylcobaltcarbonyl complex of the formula: STR3 wherein R1 and R2 are as defined above, reacting the acylcobaltcarbonyl complex thus formed with carbon monoxide and an alkali metal hydroxide or an alkaline earth metal hydroxide at elevated temperature and elevated pressure in a liquid solvent medium to form the corresponding alkali metal salt or alkaline earth metal salt of the product α-keto-carboxylic acid and thereafter acidifying the salt of the α-keto-carboxylic acid to form the product α-keto-carboxylic acid.
Preparation of α-keto-carboxylic acids from acyl halides
-
, (2008/06/13)
A process for the production of α-keto-carboxylic acids of the general formula: STR1 wherein R1 and R2 are the same or different and are hydrogen, hydrocarbyl radicals, substituted hydrocarbyl radicals or hydrocarbyloxy radicals by reacting an acyl halide of the formula: STR2 wherein R1 and R2 are as defined above and X represents halogen, in a liquid solvent medium, with an alkali metal tricarbonyl[triphenylphosphine]cobaltate complex of the formula: wherein M is an alkali metal to form the corresponding phenylacetyl tricarbonyl[triphenylphosphine]cobalt complex of the formula: STR3 wherein R1 and R2 are as defined above, reacting the acylcobaltcarbonyl complex thus formed with carbon monoxide and an alkali metal hydroxide or an alkaline earth metal hydroxide at elevated temperature and elevated pressure in a liquid solvent medium to form the corresponding alkali metal salt or alkaline earth metal salt of the product α-keto-carboxylic acid and thereafter acidifying the salt of the α-keto-carboxylic acid to form the product α-keto-carboxylic acid.
Kinetics of the Pyridoxal-Catalyzed Dealdolation and β Elimination of Some Aromatic β-Hydroxy α-Amino Acids
Marcello, Joseph,Martell, Arthur E.
, p. 3441 - 3447 (2007/10/02)
The rates of dealdolation and β elimination of a number of para-substituted phenylserines have been determined by proton NMR.Electron-withdrawing substituents on the amino acid side chain enhance the dealdolation rate.In the substituted phenylserine β elimination and dealdolation were found to occur as parallel reactions.The metal ion-pyridoxal catalyzed systems undergo reaction more rapidly than the metal-free pyridoxal-catalyzed systems.A reaction mechanism for the parallel dealdolation and β-elimination reactions is proposed.In the case of one of the amino acids, phenylthreonine, the rate constants for the metal-free Schiff base were resolved into the specific rate constants for the individual solution components, and the variations obtained for the specific rate constants are interpreted in terms of the proposed reaction mechanism.
