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Collect. Czech. Chem. Commun. 2009, 74, 1179-1193
https://doi.org/10.1135/cccc2009025
Published online 2009-08-11 16:51:29

Biotransformations of morphine alkaloids by fungi: N-demethylations, oxidations, and reductions

Vigi Chaudharya, Hannes Leischa, Alena Moudraa, Blake Allena, Vincenzo De Lucaa, D. Phillip Coxb and Tomáš Hudlickýa,*

a Department of Chemistry and Centre for Biotechnology, Brock University, 500 Glenridge Avenue, St. Catharines ON L2S 3A1, Canada
b Noramco Inc., 503 Carr Road, Suite 200, Wilmington, DE 19809, USA

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  • Gallagher Ryan, Chebib Mary, Balle Thomas, McLeod Malcolm D.: Thiol-Reactive Analogues of Galanthamine, Codeine, and Morphine as Potential Probes to Interrogate Allosteric Binding within Nicotinic Acetylcholine Receptors. Aust. J. Chem. 2015, 68, 1834. <https://doi.org/10.1071/CH15475>
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  • Kok Gaik B., Scammells Peter J.: N-Demethylation of N-methyl alkaloids with ferrocene. Bioorganic & Medicinal Chemistry Letters 2010, 20, 4499. <https://doi.org/10.1016/j.bmcl.2010.06.031>
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