Hydrophobic vitamin B12. 8. Carbon-skeleton rearrangement reactions catalyzed by hydrophobic vitamin B12 in octopus azaparacyclophane

Yukito Murakami, Yoshio Hisaeda, Teruhisa Ohno

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Abstract

Heptapropyl cobyrinate perchlorate catalyzed the carbon-skeleton rearrangements, which convert 2-acetyl-2-ethoxycarbonylpropane, 2-cyano-2-ethoxycarbonylpropane, 1-acetyl-1-ethoxycarbonylethane, and diethyl β-methyl-dl-aspartate into 1-acetyl-2-ethoxycarbonylpropane, 2-cyano-1-ethoxycarbonylpropane and 1-cyano-2-ethoxycarbonylpropane, 1-acetyl-2-ethoxycarbonylethane, and diethyl glutamate, respectively, in an octopus cyclophane placed in aqueous carbonate buffer (pH 7.0) at 20.0°C by utilizing vanadium trichloride as a cocatalyst under aerobic photolysis conditions. The migratory aptitude of the electron-withdrawing groups was found to follow the sequence: CN ≈ CO2C2H5 < COCH3. Yields of the rearrangement products were very low in the absence of heptapropyl cobyrinate perchlorate.

Original languageEnglish
Pages (from-to)49-62
Number of pages14
JournalBioorganic Chemistry
Volume18
Issue number1
DOIs
Publication statusPublished - Jan 1 1990

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All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Biology
  • Drug Discovery
  • Organic Chemistry

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