Cunninghamella echinulata

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

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.

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. 

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

Acronycine 0 0CH3 Cunninghamella echinulata NRRL 3655 Cunninghamella bainieri ATCC 9244 Aromatic hydroxylation [25]... 

Yang, W. and Davis, P.J. (1992) Microbial models of mammalian metabolism biotransformation of N-methylcarbazole using the fungus Cunninghamella echinulata. Drug Metabolism and Disposition The Biological Fate of Chemicals, 20, 58 46. 

Microbial transformations of ellipticine (15) and 9-methoxyellipticine (16) were reported by Chien and Rosazza (143, 144). Of 211 cultures screened for their abilities to transform 9-methoxyellipticine (16), several, including Botrytis alii (NRRL 2502), Cunninghamella echinulata (NRRL 1386), C. echinulata (NRRL 3655), and Penicillium brevi-compactum (ATCC 10418), achieved O-demethylation of 16 in good yield (Scheme 9). P. brevi-compactum was used to prepare 9-hydroxyellipticine (22) from the methoxylated precursor, and 150 mg of product was obtained from 400 mg of starting material (37% yield). The structure of the metabolite was confirmed by direct comparison with authentic 9-hydroxyellipticine (143). O-Demethylation is a common microbial metabolic transformation with 16 and many other alkaloids (143). Meunier et al. have also demonstrated that peroxidases catalyze the O-demethylation reaction with 9-methoxyellipticine (145). 

Deisopropylation (Cunninghamella echinulata, Gliocladium deliquescens) and oxidation to carboxylic acid (G. deliquescens)... 

Allylic methyl group hydroxylation and oxidation to carboxylic acid Beauveria bassiana) Allylic methyl group hydroxylation and lactate ester formation glucosidation Cunninghamella echinulata)... 

Phenazo- pyridine Analgesic HaN v) NHa 35 2 -, 4 - and 5-hydro-xylations cleavage to 4-aminophenol, followed by N-acetylation 4 -Hydroxylation and 4 -0-sulfate conjugation (Cunninghamella echinulata) [98]... 

C-7 Hydroxylation and D-ring (unidentified position) hydroxylation Cunninghamella echinulata, Beauveria bassiana)... 

Schilling, R., G. Engelhardt, and P.R. Wallnofer (1985). Degradation of the herbicide metribuzin (Sencor) by pure cultures of Cunninghamella echinulata Thaxter ATCC 38447. Chemosphere, 14 267-270. 

In a major study of the microbial metabolism of acronycine (177), Rosazza and co-workers examined 47 cultures for their capacity to transform this alkaloid, 10 of which were active in producing metabolites more polar than the starting material. The major metabolite was identified as the 9-hydroxy derivative 177 following isolation from the incubation of 176 with Cunninghamella echinulata NRRL 3655. This product was characterized as the acetate 182 by MS and PMR analysis, the latter technique... 

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