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

Authors
  • 1
  • 2
  • 3
Type
Published Article
Journal
Nature Chemical Biology
1552-4469
Publisher
Nature Publishing Group
Publication Date
Volume
11
Issue
2
Pages
104–106
Identifiers
DOI: 10.1038/nchembio.1717
PMID: 25485687
Source
Medline

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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