Acetylation serves as a protective group in noscapine biosynthesis in opium poppy

December 8th, 2014 by Thu-Thuy T Dang

Nature Chemical Biology 11, 104 (2015). doi:10.1038/nchembio.1717

Authors: Thu-Thuy T Dang, Xue Chen & Peter J Facchini

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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