Steroid hydroxylation by Whetzelinia sclerotiorum, Phanerochaete chrysosporium and Mucor plumbeus

Predominant allylic hydroxylation at carbons 6 and 7 of 4 and 5-ene functionalized steroids by the thermophilic fungus Rhizomucor tauricus IMI23312

“…6␤ or 7␤) stereochemical configuration was the predominant respective steroidal transformation for the 4-ene and 5-ene molecules however; in two cases (2,14) it was non-stereospecific giving rise to both ␣,␤-epimers. Similar fungal metabolic handling of the tested substrates has been observed in a wide range of non-thermophilic fungi with 4-ene [22][23][24] and 5-ene containing steroids [20,21,23,[25][26][27][28][29]. Interestingly, allylic oxidation of progesterone (1) at C-6 has been observed in two species of thermophilic Bacilli [5,30], however, side-chain degradation and reductive transformation observed in both thermophilic Bacilli and non-thermophilic fungi [5,31,32] were not detected.…”

Identification and partial characterization of Rhizopus nigricans Gβ proteins and their expression in the presence of progesterone

“…Progesterone, for example, is predominantly transformed into products hydroxylated at different positions, e.g. 11␣-by R. nigricans [3] and Aspergillus ochraceus [4], 15␣-by Fusarium culmorum [5], Acremonium strictum [6] and Fusarium oxysporum [7] and 7␣/11␤-and 6␤/11␣-by Mucor plumbeus [8]. These hydroxylation reactions constitute a common way of increasing the water solubility of hydrophobic compounds, which can then be excreted to the surroundings.…”

Chemical Synthesis of Uncommon Natural Bile Acids: The 9α-Hydroxy Derivatives of Chenodeoxycholic and Lithocholic Acids

“…[6][7][8] This synthetic method can be used to prepare chemical structures that are difficult to obtain by ordinary chemical methods. The observed biotransformations may suggest metabolic pathways in mammals, due to similarity between mammalian and microbial systems.…”