Microbial C-hydroxylation and β-4-O-methylglucosidation of methyl-benzamide 7-azanorbornane ethers with Beauveria bassiana

Horacio F. Olivo, Tonya L. Peeples, María Yolanda Ríos, Francisco Velázquez, Jin Woo Kim, Someet Narang

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Abstract

N-Substituted 7-azanorbornanes were prepared by acylation of easily accessible 7-azanorbornane hydrochloride. Derivatives possessing an electron-withdrawing docking/protecting group and bearing an aryl methylether were subjected to biotransformation with the fungus Beauveria bassiana ATCC 7159. O-Demethylation and β-4-O-methylglucosidation reactions were observed for the major metabolite in this biotransformation (isolation yields: 6, 30%; 11a, 44%; 11b, 47%; 11c, 14%). C-Hydroxylation on an unfunctionalized carbon was also observed in most of the cases.

Original languageEnglish (US)
Pages (from-to)97-105
Number of pages9
JournalJournal of Molecular Catalysis B: Enzymatic
Volume21
Issue number3
DOIs
Publication statusPublished - Jan 16 2003

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All Science Journal Classification (ASJC) codes

  • Catalysis
  • Bioengineering
  • Biochemistry
  • Process Chemistry and Technology

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