Bacillus subtilis var. niger

Some strains produce glycerol TAs with 2,3-diesterlinkages, e.g. the teichoic acid from Bacillus subtilis var. niger WM, 2> shown below ... 

Recently, the synthesis of l-deoxy-3-O-phosphono-D-glycerol-l-yl-P-D-gluco-pyranoside disodium salt 27 and its L-glycerol-l-yl isomer 31 was described 45). Compound 27 is a repeating unit of TA chains from Bacillus subtilis var. niger WM (formula 3). Both 27 and 31 were obtained mainly to record their l3C-NMR spectra to be further compared with the spectrum of the naturally occurring teichoic acid. Thus, 27 was prepared in a few-step synthesis as shown below ... 

The micro-organism Bacillus subtilis var. Niger will hydrolyse preferentially one enantiomer of ( )-alkylcyclohexanol acetate.26 In this way, treatment of ( )-a-cyclogeranyl acetate (45) gave (— )-(S)- -cyclogeraniol, together with ( + )-(R)-a-cyclogeranyl acetate, in low optical purity. 

Mohn, G. Ostlund, K. Dry-heat inactivation of Bacillus subtilis var. niger spores with special reference to spore density. Can. J. Microbiol. 1976, 22, 359. 

The effects of EtO concentration and process temperature were widely studied. Ernst and Shull initially verified that the lethality kinetics of Bacillus subtilis var. niger spores is of zero order at high levels of EtO. With the EtO concentration reduction, the reaction becomes first order. Its sterilization curves at different temperatures show the required EtO concentration, and the duplication of the reaction rate of every 10°C. 

FIGURE 19.104 Microbial resolution of carvomenthols by Trichoderma S and Bacillus subtilis var. niger. (Modi ed from Oritani, T. and Yamashita, K Agric. Biol. Chem., 37, 1691, 1973d.)... 

Microbial resolution of carvomenthols was carried out by selected microorganisms such as Trichoderma S and Bacillus subtilis var. niger (Oritani and Yamashita, 1973d). Racemic carvo-menthyl acetate, racemic isocarvomenthyl acetate, and racemic neoisocarvomenthyl acetate were asymmetrically hydrolyzed to (-)-carvomenthol (49b ) with (+)-carvomenthyl acetate, (-)-isocarvomenthol (49c) with (+)-isocarvomenthyl acetate, and (+)-neoisocarvomenthol (49d ) with (-)-neoisocarvomenthyl acetate, respectively racemic neocarvomenthyl acetate was not hydrolyzed (Oritani and Yamashita, 1973d) (Figure 14.104). 

My first paper in chemoenzymatic synthesis appeared in the fall of 1978 under the title "Synthesis of optically active alkynyl alcohols by microbial asymmetric hydrolysis of the corresponding acetates" [2,3]. As shown in Figure 24.1, asymmetric hydrolysis of ( )-l with Bacillus subtilis var. niger was only moderately successful, yielding the recovered (1 )-1 and the hydrolyzed (S)-2 of 7-96% ee [2, 3]. After 35 years of cooperative endeavor by biochemists as the suppliers of enz5unes and synthetic chemists as the users, it is now possible to employ various lipases and esterases as commercially available and bottled reagents for enantioselective synthesis of natural products, pharmaceuticals, and agrochemicals. 

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