Nicotinamide Rhodococcus rhodochrous

Nicotinamide 10 Nicotinamide Treatment of pellagra Hydrolysis Rhodococcus rhodochrous Immobilized cells [7]... 

As mentioned in Chapter 1 the same Rhodococcus rhodochrous catalyses the last step in Lonza s >3500 tonnes/year nicotinamide synthesis [94, 111, 112]. Lonza has further developed this technology and currently synthesises a number of relevant fine chemical building blocks with nitrile hydratases [94, 113]. 

Nagasawa, T., Mathew, C.D., Manger, 1., et al. 1988. Nitrile hydratase-catalysed prodnction of nicotinamide from 3-cyanopyridine in Rhodococcus rhodochrous 11. Applied and Environmental Microbiology, 54 1766-9. 

Prasad, S., Raj, 1., and Bhalla, T.C. 2007. Bench scale conversion of 3-cyanopyridine to nicotinamide using resting cells of Rhodococcus rhodochrous PA-34. Indian Journal of Microbiology, 47 34 1. 

Rhodococcus sp. N-774 and Pseudomonas chlororaphis B23 resting cells have been used at industrial scale (as first- and second-generation biocatalysts) for the biological production of acrylamide from acrylonitrile since the 1980s [21]. Currently Rhodococcus rhodochrous J1 is being adopted as a third-generation biocatalyst (Mitsubishi Rayon Co.). The industrial production of nicotinamide from 3-cyanopyridine is also operated with this strain (Lonza AG). However, despite the enormous potentiality of nitrile-hydrolyzing biocatalysts for industrial applications, only a few commercial processes have been realized [22]. 

Acrylamide (Ch) Nicotinamide (H) Nitrile hydratase Rhodococcus rhodochrous... 

Production of acrylamide (Fig. 13) by hydration of acrylonitrile under the action of the intracelluar nitrile hydratase in Rhodococcus rhodochrous (Nitto Chemical Industry Co., Ltd., fed-batch process). The annual production amounts to >30000 tons (see also Table 6). Acrylamide is one of the most important commodity chemicals and is required in large quantities as the pre-polymer of polyacrylamide that is widely used in polymer and floccu-lent applications. The advantages of this hydratase approach in comparison with the classical chemical nitrile hydration are higher product end concentration, quantitative yields, no formation of acrylic acid, no need for copper catalyst, and only five chemical/technical operations instead of seven [73,112,113,171]. An analogous process for nicotinamide is being commercialized by Lonza (see also section 6). 

The production of amides from nitriles has been studied by several workers, and most of them focused on the accumulation of acetamide from acetonitrile [126,133-136]. The enz3nnatic production of acrylamide from acrylonitrile by nitrile hydratase of P. chlororaphis B23, Rhodococcus sp. N-774, and Klebsiella pneumoniae, respectively has been reported [137-142]. These microorganisms exhibited a high nitrile hydratase activity and a low amidase activity, allowing the accumulation of the corresponding amide. Nagasawa et al. optimized the reaction conditions for the production of nicotinamide by a nitrile hydratase, found in Rhodococcus rhodochrous Jl. The enzyme contains cobalt, and shows high activity towards 3-cyanopyridine [143,144]. 

Lonza Fine Chemicals manufactures nicotinamide by a process in which 2-methyl-l,5-diaminopentane (a by-produa of nylon-6,6 manufacture) is first converted to 3-cyanopyridine 121 by a series of three chemically-catalyzed reactions, then the nitrile is hydrated to nicotinamide 122 (Figure 11.37) using Rhodococcus rhodochrous Jl cells immobilized in polyacrylamide particles [227-229]. A continuous feed of 3-cyanopyridine at concentrations of between 10-20 Avt /o is added in the direction of process flow, with a counter-current feed of biocatalyst in a series of stirred-tank batch bioreactors. The process generates... 

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