Nocardia salmonicolor

Pseudomonas sp. strain (PL) was cultivated with p-cymene (178) as the sole carbon source to give cumyl alcohol (192), cumic acid (194), 3-hydroxycumic acid (196), 2,3-dihydroxycumic acid (197), 2-oxo-4-methylpentanoic acid (201), 9-hydroxy-p-cymene (189), and p-cymene-9-oic acid (190) as shown in Figure 19.55 (Madyastha and Bhattacharyya, 1968). On the other hand, p-cymene (178) was converted regiospeci cally to cumic acid (194) by Pseudomonas sp.. Pseudomonas desmolytica, and Nocardia salmonicolor (Madyastha and Bhattacharyya, 1968) (Figure 19.56). 

FIGURE 19.56 Biotransformation of />-cymene (178) to cumic acid (194) by Pseudomonas sp. Pseudomonas desmolytica, and Nocardia salmonicolor. (Modi ed from Yamada, K. et al., Agric Biol. Chem., 29,943,1965 Madyastha, K.M. and Bhattacharyya, P.K., Indian J. Biochem., 5,161,1968- Noma Y. 2000. unpublished data.)... 

The benzazepinone 59 was designed and tested as a more potent and a longer lasting analog of diltiazem, the benzothiazepinone calcium blocker of wide use in the treatment of hypertension and angina. Synthesis of 59 (Scheme 22) required the preparation of 58, which was prepared by microbial reduction of the dione 57. Due to the rapid equilibration of the latter compound, the reduction to one single enantiomer with microorganisms was possible. Thus compound 58 was obtained in optimized condition at 2 g/L in 96% yields and 99.9 e.e. with cultures of Nocardia salmonicolor [110]. 

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