Sporotrichum sulfurescens

N-benzoylated cyclic amines and bicyclic amines undergo transannular hydroxylation when incubated with Sporotrichum sulfurescens. 1-Ben-zoylpiperidine is converted into l-benzoyl-4-hydroxypiperidine in approximately 20% yield [1081]. A -Benzoylhexamethyleneimine gives 4-hydroxy-3-keto and 4-keto derivatives as a result of transannular hydroxylation and subsequent oxidation (equation 516). 

The microbiological oxidation of coronaridine (229) by means of Sporotrichum sulfurescens affords a phenolic derivative (230) of uncertain orientation, together with a lactam (231) identical with an alkaloid previously isolated from Conopharyn-gia jollyana Stapf., and a hydroxylactam, provisionally formulated as (232). The action of Cunninghamella blakesleana Lendner leads to a hydroxycoronaridine, which is suspected to be (233). 

Models have been developed to accommodate the results of the hydroxyla-tion of substrates with different structures. The cytochrome P450CAM camphor hydroxylase from the bacterium Pseudomonas putida has been studied by X-ray crystallography. The importance of hydrophilic interactions with a valine (VAL-247) and a polar interaction mediated by hydrogen bonding to a tyrosine residue (TYR-96) has been noted. A model based on the hydroxylation of numerous cyclic amides by Beauveria sulfurescens (originally named Sporotrichum sulfurescens) showed that hydroxylation occurred preferentially at a methylene group about 5.5 A from an electron-rich substituent on the substrate. 

Sporotrichum asteroides bombycinum epigaeum gougeroti sulfurescens... 

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