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Hydroxynitrile glucosides.

Nanna Bjarnholt1, Birger Lindberg Møller

  • 1Plant Biochemistry Laboratory and The VKR Research Centre Pro-Active Plants, Department of Plant Biology and Biotechnology, Faculty of Life Sciences, University of Copenhagen, Frederiksberg C, Copenhagen, Denmark.

Phytochemistry
|June 10, 2008
PubMed
Summary
This summary is machine-generated.

Beta- and gamma-hydroxynitrile glucosides, unlike cyanogenic glucosides, do not release hydrogen cyanide. Their biosynthesis likely involves common intermediates and diversified enzymes, explaining their presence in plants.

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Area of Science:

  • Plant biochemistry
  • Metabolomics
  • Enzymology

Background:

  • Beta- and gamma-hydroxynitrile glucosides are structurally similar to cyanogenic glucosides but do not produce hydrogen cyanide.
  • Their co-occurrence suggests shared biosynthetic pathways with cyanogenic glucosides.

Purpose of the Study:

  • To propose a unified biosynthetic pathway for alpha-, beta-, and gamma-hydroxynitrile glucosides.
  • To identify key enzymes and intermediates involved in their formation.

Main Methods:

  • Literature review and data analysis.
  • Hypothesizing enzyme functions based on known pathways.
  • Comparative analysis of related glucosides.

Main Results:

  • Oximes produced by CYP79 orthologs are proposed as common intermediates.
  • Evolutionarily diversified multifunctional enzymes, designated CYP71(betagamma) and CYP71(alphabetagamma), are hypothesized to convert oximes.
  • These enzymes, along with CYP71(alpha) orthologs, can hydroxylate various positions on amino acid and oxime-derived nitriles.

Conclusions:

  • A proposed pathway involving hydroxylation, dehydration, and glycosylation explains the formation of unsaturated beta- and gamma-hydroxynitrile glucosides.
  • This scheme accounts for the distribution patterns of different hydroxynitrile glucosides in plants.
  • The study discusses potential biological roles of these hydroxynitriles.