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

doi:10.1016/S1381-1177(02)00081-4

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 journal › Article

18 Scopus citations

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 language	English (US)
Pages (from-to)	97-105
Number of pages	9
Journal	Journal of Molecular Catalysis B: Enzymatic
Volume	21
Issue number	3
DOIs	https://doi.org/10.1016/S1381-1177(02)00081-4
Publication status	Published - Jan 16 2003

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All Science Journal Classification (ASJC) codes

Catalysis
Bioengineering
Biochemistry
Process Chemistry and Technology

Cite this

Olivo, H. F., Peeples, T. L., Ríos, M. Y., Velázquez, F., Kim, J. W., & Narang, S. (2003). Microbial C-hydroxylation and β-4-O-methylglucosidation of methyl-benzamide 7-azanorbornane ethers with Beauveria bassiana. Journal of Molecular Catalysis B: Enzymatic, 21(3), 97-105. https://doi.org/10.1016/S1381-1177(02)00081-4

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

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 journal › Article

TY - JOUR

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

AU - Velázquez, Francisco

AU - Kim, Jin Woo

AU - Narang, Someet

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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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10.1016/S1381-1177(02)00081-4