Mortierella isabellina

FIGURE 2.1 Biotransformation of dehydroabietic acid by Mortierella isabellina. 

Microbiological oxidation is the easiest procedure because it uses the intact cells. Scheme 6C. 11 shows results obtained by using Aspergillus Niger [101], Enantioselectivity can be very high but experiments are performed on a small scale, which results in a low yield of sulfoxides. Both enantiomers of methyl p-tolyl sulfoxide were prepared by Sih et al. with Mortierella isabellina NRRL 1757, giving (/ )-sulfoxide with 100% ee in 60% yield or with Helminthosporium sp NRRL 4671, giving (S)-sulfoxide with 100% ee in 50% yield [104], A similar result was obtained for ethyl p-tolyl sulfide. A predictive model for sulfoxidation by Helminthosporium sp NRRL 4671 was proposed by Holland et al. [105], which was based on the analysis of more than 90 biotransformations of sulfides. 

The transformation of chroman-4-ones into (S)-chroman-4-ols by Mortierella isabellina has been applied to naphtho[2,3-b]pyran-4-one to provide a synthesis of naturally occurring (S)-4-hydroxy-lapachone (95CJC1399) and various chroman-4-ones have been enantioselectively reduced by NaBTLt in the presence of optically active Co (II) complexes (95AG(E)2145). 

Lactobacillus kefir alcohol dehydrogenase, NADPH Mortierella isabellina... 

Forskolin derivatives, for example (50), can be hydroxylated by, for example, Neurospora crassa (ATCC 10336), Mortierella isabellina (ATCC 160074) and Aspergillus niger (DSM 3210) 2a-, 2P-, 3o- or 3P-hydroxy derivatives can be obtained in this way (e.g. equation 15). ... 

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). ... 

Oxidation ofSuffur, Selenium and Tellurium Mortierella isabellina NRRL 1757,40 h... 

The fungus Mortierella isabellina (NRRL 17S7) hydroxylates the ethylbenzenes (92) to the 1-arylelha-nols (93 equation 32) with a degree of enantioselectivity as shown in Table 9. By-products resulting from teiminal carbon hydroxylation and overoxidation (acetophenones) are also obtained. 

Efficient oxidation also results from treatment of cyclopropyl phenyl sulfide (7) with ( —)-camphorsulfonyloxaziridines 8. Due to the optical activity of the reagents, the product cyclopropyl phenyl sulfoxide 9 is optically active. The best results were obtained when (-)- , -dichlorocamphorsulfonyloxaziridine [( —)-8b] was used the sulfoxide was obtained in 90% yield with 92% ee of the 5 -isomer. Application of ( —)-camphorsulfonyloxaziridine ( —)-8a, on the other hand, lowered both the yield and the enantiomeric excess to 23%.Moderate optical purity was obtained when cyclopropyl phenyl sulfide was incubated with Mortierella isabellina, cyclopropyl phenyl sulfoxide was isolated in 58% yield with 66%ee of the (-1-)-sulfoxide, together with cyclopropyl phenyl sulfone (2% yield). Optically inactive cyclopropyl phenyl sulfoxide was obtained in 98% yield when the corresponding sulfide was treated with sodium metaperiodate. ... 

Kutney, J.P., E. Dimitriadis, G.M. Hewitt, P.J. Salisbury, and M. Singh. 1982. Studies related to biological detoxification of kraft mill effluent. IV—The biodegradation of 14-chlorodehydroabietic acid with Mortierella isabellina. Helv. Chem. Acta 65 1343-1350. 

Thus, benzocycloalkenes have been described to undergo bacterial hydroxylation by the Pseudomonas putida strain UV4. As shown in Fig. 16.1-15, this yielded exclusively hydroxylation at the benzylic position, and also one single enantiomer, i.e. the (R)-alcohol. The biotransformation of benzocyclobutene proved, however, to be different from that observed for higher benzocycloalkenes, presumably because of its particular chemical reactivity 77. A similar result has been observed by Holland and coworkers in the course of chroman biotransformation by the fungus Mortierella isabellina[78 which leads, although in low yield, to the benzylic (R)-alcohol. 

Holland et al.1181 obtained the (R)-sulfoxides from various para-substituted phenyl 3-chloropropyl and phenyl 3-hydroxypropyl sulfides by biotransformation with the fungus Mortierella isabellina with an enantiomeric excess of 82-88%. The (S)-sulfoxides were produced using the fungus Helminthosporium sp. and the bacterium Acinetobacter calcoaceticus with ee values of > 95% and 94%, respectively. 

Pentane-2,4-dione is reduced with Mortierella isabellina in 99% ee to (.S )-4-hydroxv-2-pen-tanone. If the incubation time is prolonged, the (2S.4S)-2.4-diol is obtained in 99% ee192. 

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