Carbethoxylation of coordinated histidine by diethylpyrocarbonate

J Inorg Biochem. 1993 Sep;51(4):727-35. doi: 10.1016/0162-0134(93)85005-s.

Abstract

The metastable, reversible carbethoxylation of histidine in the cobalt(III) complexes (ethylene-diamine)(histidine)chlorocobalt(III) chloride, [Co(III)(en)ClHis]Cl, and (diethylenetriamine) (histidine)cobalt(III) dichloride, [Co(III)(dien)His]Cl2, following reaction with diethylpyrocarbonate, was observed using UV spectroscopy. These observations indicate that diethylpyrocarbonate can react with a coordinated imidazole ring. CD transitions associated with coordinated carbethoxyhistidine in [Co(III)(en)ClHis]Cl and [Co(III)(dien)His]Cl2 were also observed. The molar ellipticities of the CD bands observed for carbethoxy [Co(III)(en)ClHis]Cl or carbethoxy [Co(III) (dien)His]Cl2 are much larger than the molar ellipticities of the CD transition associated with carbethoxy N alpha-acetyl-L-histidine, indicating that loss of rotational freedom of the imidazole ring could be a major factor in the enhanced CD.

Publication types

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

MeSH terms

  • Circular Dichroism
  • Cobalt / chemistry
  • Diethyl Pyrocarbonate / chemistry*
  • Histidine / chemistry*
  • Imidazoles / chemistry*
  • Models, Molecular
  • Rotation

Substances

  • Imidazoles
  • Cobalt
  • Histidine
  • Diethyl Pyrocarbonate