312-44-7Relevant academic research and scientific papers
New enzymatic methods for the synthesis of primary α-aminonitriles and unnatural α-amino acids by oxidative cyanation of primary amines with d-amino acid oxidase from porcine kidney
Kawahara, Nobuhiro,Yasukawa, Kazuyuki,Asano, Yasuhisa
supporting information, p. 418 - 424 (2017/08/14)
Oxidation of amino groups in amines or amino acids activates the sp3 Cα-H bond to form imines, making the alpha carbon atom a preferable target for nucleophilic reagents such as cyanide. Therefore, we focused on the oxidase reaction for the production of primary α-aminonitriles via imines. d-Amino acid oxidase from porcine kidney (pkDAO) and l-amino acid oxidase from Crotalus atrox catalyzed the synthesis of 2-amino-2-cyano-3-phenylpropanoic acid from phenylalanine and potassium cyanide (KCN). Mutant pkDAO (Y228L/R283G) catalyzed the synthesis of racemic-2-methyl-2-phenylglycinonitrile from (R)-α-methylbenzylamine and KCN. Based on these results, we developed a new cascade reaction for the synthesis of unnatural α-amino acids from primary amines using mutant pkDAO and nitrilase AY487533. This is the first report of the enzymatic synthesis of primary α-aminonitriles and unnatural α-amino acids. These methods will contribute widely to the synthesis of primary α-aminonitriles and unnatural α-amino acids in aqueous systems.
Water soluble phosphines: Part XIII. Chiral phosphine ligands with amino acid moieties
Brauer, David J.,Schenk, Stefan,Ro?enbach, Stefan,Tepper, Michael,Stelzer, Othmar,H?usler, Thomas,Sheldrick, William S.
, p. 116 - 126 (2007/10/03)
Nucleophilic phosphination of the potassium or sodium salt of the fluorophenylalanines (1a, 2a) or -glycines (3a, 4a) with potassium phosphides Ph(R)PK (R=Me, Ph) yields chiral phosphine ligands (1-7) with amino acid moieties. The X-ray structure of 3·2H2O (space group Pbca) has been determined showing a betaine type structure for the amino acid moiety. The α-methyl derivatives of the phosphinophenylglycines (10, 11) were obtained in an analogous manner as 1-7. ortho- and para-Fluoroacetophenones have been employed as starting material for the syntheses of α-[4-fluorophenyl]-α-methylglycine (9c) and its ortho-isomer (8c), the X-ray structure of its monohydrate has been determined (space group P1?). The N-acetyl (3b, 8e) and ester derivatives (3d, 8d) of 3 and 8c are accessible using standard procedures. Resolution of the diastereomeric salt 12 obtained from (S)-(+)-2-hydroxymethylpyrrolidine and racem-8e by fractionated crystallization yielded the (S,R)-isomer. The absolute configuration of (S,R)-12 was determined by X-ray structural analysis (space group P212121). Cleavage of (S,R)-12 with hydrochloric acid gave enantiopure (R)-8e [α]D20=-30.9° (c=1, CH3OH).
