Selectivity of the biooxygenation of N-phenylcarbamates by the fungus Beauveria bassiana

✍ Scribed by Sylke Pietz; Dörthe Wölker; Günter Haufe

• Book ID: 104208217
• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 761 KB
• Volume: 53
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(97)10148-x

✦ Synopsis

The biotransformation with Beauveria bassiana of syn-1,5-dimethylbicyclo[3.2, l]oct-8-yl-Nphenylcarbamate (11), its anti-isomer 13 and ¢yclooctyl-N-phenylcarbamate 31 is describod. Based on the observed hydroxylation positions and on earlier results of oxygenations using this fungus, a modified distance model for hydroxylations is proposed. The mode of binding of the substrate to the enzyme's active site depends on the intrinsic structure and electronic properties of its electron-rich group. The regio-and stereochemistry of hydroxylation, however, is determined mainly by the structure of the hydrocarbon moiety, namely by a specific gap from the anchoring group. This is represented by a distance of about 5.5 A between the oxygen directly attached to the carbocycle and hydrogens which potentially can be substituted.