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Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
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Biosynthetic studies on chlorophylls: from protoporphyrin IX to protochlorophyllide.

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Separation of monovinyl and divinyl protochlorophyllides and chlorophyllides from etiolated and phototransformed

C M Hanamoto1, P A Castelfranco

  • 1Department of Botany, University of California, Davis, California 95616.

Plant Physiology
|September 1, 1983
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Summary

A new high-pressure liquid chromatography method separates protochlorophyllide and chlorophyllide forms. This confirms divinyl protochlorophyllide transforms into unstable divinyl chlorophyllide in cucumber plants.

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Area of Science:

  • Biochemistry
  • Plant Physiology

Background:

  • Protochlorophyllide and chlorophyllide are key pigments in plant photosynthesis.
  • Separating their monovinyl and divinyl forms is crucial for understanding their roles.
  • Previous studies suggested divinyl protochlorophyllide's phototransformation pathway.

Purpose of the Study:

  • To develop and validate a high-pressure liquid chromatography (HPLC) method for separating monovinyl and divinyl protochlorophyllide and chlorophyllide.
  • To confirm the phototransformation of divinyl protochlorophyllide to divinyl chlorophyllide in cucumber cotyledons.

Main Methods:

  • Development of an HPLC method using a silicic acid column with dodecyl residues.
  • Utilized a mobile phase containing tetrabutyl ammonium and a solvent of 70% methanol with methyl ethyl ketone.
  • Separation performed at 0 degrees C.

Main Results:

  • Successfully separated monovinyl and divinyl forms of protochlorophyllide and chlorophyllide.
  • Confirmed that divinyl protochlorophyllide is phototransformed into divinyl chlorophyllide in cucumber cotyledons.
  • Observed rapid dark-dependent disappearance of divinyl chlorophyllide.

Conclusions:

  • The developed HPLC method is effective for separating protochlorophyllide and chlorophyllide isomers.
  • The study confirms the phototransformation pathway and instability of divinyl chlorophyllide in vivo.
  • Provides a tool for further research into chlorophyll biosynthesis and degradation.