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 › peer-review

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
State	Published - Jan 16 2003

All Science Journal Classification (ASJC) codes

Catalysis
Bioengineering
Biochemistry
Process Chemistry and Technology

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10.1016/S1381-1177(02)00081-4

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@article{2bac09953cf44534a659cb233904bb0c,

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.",

author = "Olivo, \{Horacio F.\} and Peeples, \{Tonya L.\} and R{\'i}os, \{Mar{\'i}a Yolanda\} and Francisco Vel{\'a}zquez and Kim, \{Jin Woo\} and Someet Narang",

note = "Funding Information: We thank Dr. Dale Swenson (Chemistry Department, UI) for the determination of the X-ray crystal structures for metabolites 11c and 12c . We express our gratitude to Prof. J.P.N. Rosazza for useful insights in this project. This work was supported by a Bioscience Initiative Grant at the University of Iowa. We thank Consejo Nacional de Ciencia y Tecnolog{\'ı}a (CONACyT, M{\'e}xico) for a pre-doctoral fellowship to FV and a post-doctoral fellowship to MYR. ",

year = "2003",

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day = "16",

doi = "10.1016/S1381-1177(02)00081-4",

language = "English (US)",

volume = "21",

pages = "97--105",

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TY - JOUR

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

AU - Olivo, Horacio F.

AU - Peeples, Tonya L.

AU - Ríos, María Yolanda

AU - Velázquez, Francisco

AU - Kim, Jin Woo

AU - Narang, Someet

N1 - Funding Information: We thank Dr. Dale Swenson (Chemistry Department, UI) for the determination of the X-ray crystal structures for metabolites 11c and 12c . We express our gratitude to Prof. J.P.N. Rosazza for useful insights in this project. This work was supported by a Bioscience Initiative Grant at the University of Iowa. We thank Consejo Nacional de Ciencia y Tecnologı́a (CONACyT, México) for a pre-doctoral fellowship to FV and a post-doctoral fellowship to MYR.

PY - 2003/1/16

Y1 - 2003/1/16

N2 - 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.

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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U2 - 10.1016/S1381-1177(02)00081-4

DO - 10.1016/S1381-1177(02)00081-4

M3 - Article

AN - SCOPUS:0346485691

SN - 1381-1177

VL - 21

SP - 97

EP - 105

JO - Journal of Molecular Catalysis B: Enzymatic

JF - Journal of Molecular Catalysis B: Enzymatic

IS - 3

ER -

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

Abstract

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