Corynebacterium equi

Daunomydn Daunomydnol 7-Deoxydaunomy- cinone Corynebacterium equi Mucor spinosus Streptomyces stetfisburgensis... 

Corynebacterium equi 9-a-hydroxy-3-oxo-23,24-dinorchola-4,17-diene-22-oic add Mitsubishi... 

The hydrolysis of seven alkyl arenesulfinylalkanoates by the bacterium Corynebacterium equi IFO 3730 studied by Ohta and coworkers34 are recent examples of kinetic resolutions which give sulfoxides of high enantiomeric purity and in reasonable yield. Compounds 16a, 16b and 16c were recovered in 30 to 43% yield and in 90 to 97% e.e. The S enantiomers underwent hydrolysis more rapidly than the R isomers. Sulfoxide 17 was isolated in 22% yield and 96% e.e., but sulfoxide 18 was completely metabolized. Esters other than methyl gave inferior results. The acids formed upon hydrolysis, although detected, were for the most part further metabolized by the bacterium. 

Enzyme-mediated hydrolysis of some racemic co-arenesulfinylalkanoic methyl esters, ArSO(CH2) COOMe, using Corynebacterium equi has led to a kinetic resolution in which the unreacted sulfinyl esters are enriched in one enantiomer at the sulfoxide center49. The enantiomeric purity of unreacted sulfinyl acetates and propionate ranges from 90 to 97%. 

Even entrapment of entire cells within reversed micelles without loss of their functionality has been achieved. For example, mitochondria and bacteria (Actinobacter cal-coaceticus, Escherichia coli, Corynebacterium equi) have been successfully solubilized in a microemulsion consisting of isopropyl pahnitate, polyoxyethylene sorbitan trioleate [162], Enhanced hydrogen photoproduction by the bacterium Rhodopseudomonas sphaeroides or by the coupled system Halobacterium halobium and chloroplasts organelles entrapped inside the aqueous core of reversed micelles with respect to the same cells suspended in normal aqueous medium has been reported [183,184],... 

Enantiomerically pure alkyl aryl sulfoxides have been obtained by the microbial oxidation of the corresponding sulfides (Holland 1988). Both Corynebacterium equi, and fungi... 

Ohta and coworkers used a bacterium, Corynebacterium equi IFO 3730, rather than a fungus, to oxidize eight alkyl phenyl and p-tolyl sulfides to their respective sulfoxides (119, 120) of configuration R. Virtually all of the sulfur compounds were accounted for as the sum of uncreacted sulfide, sulfoxide and sulfone. The enantiomeric purities of the sulfoxides obtained were quite good and are shown below in parentheses. The formation of the allyl sulfoxides in high optical purity is noteworthy. The authors believe that the sulfoxides were formed by enantioselective oxidation of the sulfides rather than by enantioselective oxidation of racemic sulfoxides, since the yield of sulfoxides was greater than 50% in five of the ten oxidations reported (see also Reference 34). 

Corynebacterium equi IF0 3730 gave high enantioselectivity in the oxidation of aryl alkyl sulfides [106], The results listed in Scheme 6C, 11 arise from experiments with no formation of sulfone, which occurs quite easily in several cases. Thio ketals and thio acetals were oxidized into mono S-oxides by various fungal species with enantioselectivity up to 70% ee [107]. Corynebacterium equi was very successfully used in the oxidation of formaldehyde dithioacetals to mono S-oxide or sulfone-sulfoxide, depending on the substrates. Thus n-Bu-S-CH-S-n-Bu was transformed to n-Bu-S02-CH2-S(0)-n-Bu with more than 95% ee in 70% yield. 

Microbiological oxidation of achiral sultides to homo-chiral sulfoxides has been studied longer than have chemical methods and often gives better results. - It was reported that Mortierella isabellina NRRL 1757 converted methyl p-tolyl sulfide into (+)-(/ )-sulfoxide with 100% ee, whereas Helmintho-sporium sp. NRRL 4671 oxidized the same sulfide to (-)-(S)-sulfoxide with 100% ee (Scheme 26). Oxidation of similar sulfides by Corynebacterium equi IFO 3730 was also reported to proceed with high enantioselectivities (equation 53). ... 

Corynebacterium equi Mucor spinosus Streptomyces steffisburgensis... 

Zitzelsberger, W., W. Ziegler, and P.R. Wallnofer. 1987. Stereochemistry of the degradation of veratrylglycerol-(3-2,4-dichlorophenyl-ether, a model compound for lignin bound xenobiotic residues by Phenerochaete chrysosporium, Corynebacterium equi and photosensitized rioboflavin. Chemosphere 16 1137-1142. 

Methyl phenyl thioether with hexadecane in an aqueous culture medium of diammonium hydrogen phosphate, magnesium sulphate, traces of ferrous sulphate containing yeast extract after inoculation with Corynebacterium equi, FO 3730 and incubation during 3 days at 30°C, afforded (R)-methyl phenyl sulphoxide in quantitative yield (enantiomeric excess 75%) (ref. 181). 

---