Results
Title

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

Authors

Dang, Thu-Thuy T; Chen, Xue; Facchini, Peter J

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.

Subjects

OPIUM poppy; ACETYLATION; PROTECTIVE groups (Chemistry); NOSCAPINE; BIOSYNTHESIS; CARBOXYLESTERASES

Publication

Nature Chemical Biology, 2015, Vol 11, Issue 2, p104

ISSN

1552-4450

Publication type

Academic Journal

DOI

10.1038/nchembio.1717