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.
UR - http://www.scopus.com/inward/record.url?scp=0346485691&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0346485691&partnerID=8YFLogxK
U2 - 10.1016/S1381-1177(02)00081-4
DO - 10.1016/S1381-1177(02)00081-4
M3 - Article
AN - SCOPUS:0346485691
VL - 21
SP - 97
EP - 105
JO - Journal of Molecular Catalysis - B Enzymatic
JF - Journal of Molecular Catalysis - B Enzymatic
SN - 1381-1177
IS - 3
ER -