Formyl migration product of chanoclavine-I aldehyde in the presence of the old yellow enzyme FgaOx3 from Aspergillus fumigatus: a NMR structure elucidation

Magn Reson Chem. 2011 Oct;49(10):678-81. doi: 10.1002/mrc.2796. Epub 2011 Sep 6.


A previous study showed that together with the festuclavine synthase FgaFS, the old yellow enzyme FgaOx3 from Aspergillus fumigatus catalyzed the conversion of chanoclavine-I aldehyde to festuclavine in the biosynthesis of ergot alkaloids. In the absence of FgaFS, a mixture containing two compounds with a ratio of 7:3 was detected in the enzyme assay of FgaOx3. NMR experiments including (DQF)-COSY, HSQC, HMBC and NOESY identified their structures as E/Z isomers of N-methyl-N-[(5R,10R)-10-(2-oxo-propyl)-2,4,5,10-tetrahydrobenzo[cd]indol-5-yl]formamide and proved the migration of the formyl group at C-8 in chanoclavine I-aldehyde to N-6 in the identified products.

Publication types

  • Letter
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry
  • Aldehydes / metabolism*
  • Aspergillus fumigatus / enzymology*
  • Biocatalysis
  • Ergolines / chemistry
  • Ergolines / metabolism*
  • Magnetic Resonance Spectroscopy / standards
  • Molecular Structure
  • NADPH Dehydrogenase / metabolism*
  • Reference Standards
  • Stereoisomerism


  • Aldehydes
  • Ergolines
  • chanoclavine
  • NADPH Dehydrogenase