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

Research output: Contribution to journalArticle

18 Citations (Scopus)

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
StatePublished - Jan 16 2003

Fingerprint

Beauveria
Hydroxylation
Ethers
Biotransformation
Bearings (structural)
Acylation
Metabolites
Fungi
Carbon
Electrons
Derivatives
benzamide

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Bioengineering
  • Biochemistry
  • Process Chemistry and Technology

Cite this

Olivo, Horacio F. ; Peeples, Tonya L. ; Ríos, María Yolanda ; Velázquez, Francisco ; Kim, Jin Woo ; Narang, Someet. / Microbial C-hydroxylation and β-4-O-methylglucosidation of methyl-benzamide 7-azanorbornane ethers with Beauveria bassiana. In: Journal of Molecular Catalysis B: Enzymatic. 2003 ; Vol. 21, No. 3. pp. 97-105.
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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.",
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Microbial C-hydroxylation and β-4-O-methylglucosidation of methyl-benzamide 7-azanorbornane ethers with Beauveria bassiana. / Olivo, Horacio F.; Peeples, Tonya L.; Ríos, María Yolanda; Velázquez, Francisco; Kim, Jin Woo; Narang, Someet.

In: Journal of Molecular Catalysis B: Enzymatic, Vol. 21, No. 3, 16.01.2003, p. 97-105.

Research output: Contribution to journalArticle

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T1 - Microbial C-hydroxylation and β-4-O-methylglucosidation of methyl-benzamide 7-azanorbornane ethers with Beauveria bassiana

AU - Olivo, Horacio F.

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AU - Ríos, María Yolanda

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AB - 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.

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