In vivo and in vitro preparation of divinyl-132,173-cyclopheophorbide-a enol

Bioorg Med Chem Lett. 2018 Apr 1;28(6):1090-1092. doi: 10.1016/j.bmcl.2018.02.015. Epub 2018 Feb 9.

Abstract

Divinyl-132,173-cyclopheophorbide-a enol was in vivo produced as a metabolite of divinyl-chlorophyll-a by protists and in vitro prepared by the intramolecular cyclization of methyl divinyl-pyropheophorbide-a, one of the divinyl-chlorophyll-a derivatives. The 1H NMR spectra in CDCl3 showed that the obtained product took exclusively its enol form in the solution. The intramolecular cyclization of chlorin π-system at the C132 and C173 positions affected the optical properties of such chlorophyll derivatives including the non-fluorescent emission of the enol.

Keywords: Biodegradation; Chlorophyll catabolism; Divinyl-chlorophyll; Intramolecular cyclization.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chlorophyll / analogs & derivatives*
  • Chlorophyll / chemical synthesis
  • Chlorophyll / chemistry
  • Chlorophyll / metabolism
  • Molecular Conformation
  • Vinyl Compounds / chemistry*
  • Vinyl Compounds / metabolism

Substances

  • 13(2),17(3)-cyclopheophorbide b enol
  • Vinyl Compounds
  • divinyl chlorophyll a
  • Chlorophyll