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Updated: Apr 19, 2026

Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase
Published on: November 23, 2016
Acetylation serves as a protective group in noscapine biosynthesis in opium poppy
Thu-Thuy T Dang1, Xue Chen1, Peter J Facchini1
1Department of Biological Sciences, University of Calgary, Calgary, Alberta, Canada.
Abstract:
We have characterized four sequential enzymes that transform 1-hydroxy-N-methylcanadine to narcotoline hemiacetal, completing our elucidation of noscapine biosynthesis in opium poppy. Two cytochromes P450 catalyze hydroxylations at C13 and C8 on the protoberberine scaffold, the latter step inducing ring opening and the formation of an aldehyde moiety. Acetylation at C13 before C8 hydroxylation introduces a protective group subsequently hydrolyzed by a carboxylesterase, which triggers rearrangement to a cyclic hemiacetal.
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