Cunninghamella

Chaetomium glohosum Cladosporium cladosporiodes Colletotrichum lagenarium Cunninghamella echinulata Curvularia trifolii Fusarium episphaeria... 

Leucomycines Ai and A3 Magnamydns A and B Middamydn Corresponding 4"-0- deisovaleryl derivatives Cunninghamella elegans and other fungi Streptomyces sp. 

Carnell et al. discovered that whole cells of Cunninghamella echinulata NRRL1384 were able to deracemize racemic N-(l-hydroxy-l-phenylethyl)benzamide (24) to produce the (R) enantiomer (Figure 5.17) [30]. The deracemization involves fast, highly (S)-selective oxidation, followed by slower, partially (R)-selective reduction of the ketone (25). Optimization by removing competing extracellular amidase/prote-ase activity resulted in 82% yield and 92% ee. 

Figure 5.17 Deracemization of alcohol (24) using Cunninghamella echinulata.

Scheme 9.6 Deracemization by Cunninghamella echinulata by imperfect enzymatic interconversion.

Ferris IP, LH MacDonald, MA Patrie, MA Martin (1976) Aryl hydrocarbon hydroxylase activity in the fungus Cunninghamella bainierr, evidence for the presence of cytochrome P-450. Arch Biochem Biophys 175 443-452. 

Pothuluri JV, JP Freeman, FE Evans, TB Moorman, CE Cerniglia (1993) Metabolism of alachlor by the fungus Cunninghamella elegans. J Agric Food Chem 41 483-488. 

Seigle-Murandi FM, SMA Krivobok, RL Steiman, J-LA Benoit-Guyod, G-A Thiault (1991) Biphenyl oxide hydroxylation by Cunninghamella echinulata. J Agric Food Chem 39 428-430. 

Milanova R, M Moore, Y Hirai (1994) Hydroxylation of synthetic abietane diterpenes by Aspergillus and Cunninghamella species novel route to the family of diterpenes isolated from Tripterygium wilfordii. J Nat Prod 5T 882-889. 

FIGURE 8.19 Biotransformation of 7-methylbenz[a]anthracene by Cunninghamella elegans. 

FIGURE 8.20 Alternative pathways for the biotransformation of fluoranthene by Cunninghamella elegans. 

Cerniglia CE, DT Gibson (1979) Oxidation of benzo[a]pyrene by the filamentous fungus Cunninghamella elegans. J Biol Chem 254 12174-12180. 

Cerniglia CE, KL Lambert, DW Mille, JP Freeman (1984b) Transformation of 1- and 2-methylnaphthalene by Cunninghamella elegans. Appl Environ Microbiol 47 111-118. 

Cerniglia CE, PP Fu, SK Yang (1982c). Metabolism of 7-methylbenz[a]anthracene and 7-hydroxymethylbenz [a]anthracene by Cunninghamella elegans. Appl. Environ. Microbiol. 44 682-689. 

Cunninghamella elegans metabolized 1-fluoronaphthalene to a number of products whose synthesis was clearly initiated by the formation of epoxides and trani-dihydrodiols (Figure 9.28) (Cerniglia et al. 1984). This illustrates the apparent indifference of the monooxygenase to the presence of fluorine atoms. 

FIGURE 9.28 Transformation of 1-fluoronaphthalene by Cunninghamella elegans. (From Neilson, A.H. and Allard, A.-S., The Handbook of Environmental Chemistry, Vol. 3R, Springer Verlag, 2002, pp. 1-74. With permission.)... 

Papavarine H3CO Aspergillus alliaceus NRRL 315 Cunninghamella echinulata ATCC 9244 0 dealkylation [24]... 

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