Rhodococcus rhodochrous IFO

The NHase and amidase from Rhodococcus rhodochrous IFO 15 564 was studied using a series of a,a-disubstituted malononitriles. This amidase preferentially hydrolyzes the pro (R) amide of the prochiral di-amide, which is an intermediate resulting from the nonenantiotopic NHase activity on the dinitrile substrate. This transformation was combined with a Hofmann rearrangement to generate a key precursor of (A)-methyldopa in 98.2% ee and 95% yield (Figure 8.5) [41],... 

Matoishi, K. Sano, A. Imai, N. Yamazaki, T. Yokoyama, M. Sugai, T. Ohta, H. Rhodococcus rhodochrous IFO 15564-mediated hydrolysis of alicyclic nitriles and amides stereoselectivity and use for kinetic resolution and asymmetri-zation. Tetrahedron Asymmetry 1998, 9, 1097-1102. 

Biotransformation can serve as an alternative route towards enantiopure aziridines. (1R,25)-1 -Benzyl- and l-arylaziridine-2-carboxamides were obtained in enantiomerically pure form via kinetic resolution of their racemates by Rhodococcus rhodochrous IFO 15564 catalyzed hydrolysis <07OF521>. Rhodococcus erythropolis AJ270 was reported as an efficient whole cell catalyst for the synthesis of highly enantiopure 5,-l-arylaziridine-2-carboxamides and A-l-arylaziridine-2-carboxylic acids <07JOC2040>. Enantiopure 2-... 

Kashiwagi M, Fuhshuku K-1, Sugai T (2004) Control of the nitrile-hydrolyzing enzyme activity in Rhodococcus rhodochrous IFO 15564 preferential action of nitrile hydratase and amidase depending on the reaction condition factors and its application to the one-pot preparation of amides from aldehydes. J Mol Catal B Enzym 29(l-6) 249-258... 

Figure 25 Preparation of (5)-2-arylpropionic acids and (iiI)-2-arylpropionamides from the corresponding racemic nitriles by (5)-specific amidases from a Rhodococcus equi TG 328 and Rhodococcus rhodochrous IFO 15564.

Figure 26 Racemic resolution and asymmetric synthesis catalyzed by a stereospecific amidase from Rhodococcus rhodochrous IFO 15564.

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