Stabilisation of methylene radicals by cob(II)alamin in coenzyme B12 dependent mutases

Chemistry. 2005 Dec 23;12(2):352-62. doi: 10.1002/chem.200501074.

Abstract

Coenzyme B12 initiates radical chemistry in two types of enzymatic reactions, the irreversible eliminases (e.g., diol dehydratases) and the reversible mutases (e.g., methylmalonyl-CoA mutase). Whereas eliminases that use radical generators other than coenzyme B12 are known, no alternative coenzyme B12 independent mutases have been detected for substrates in which a methyl group is reversibly converted to a methylene radical. We predict that such mutases do not exist. However, coenzyme B12 independent pathways have been detected that circumvent the need for glutamate, beta-lysine or methylmalonyl-CoA mutases by proceeding via different intermediates. In humans the methylcitrate cycle, which is ostensibly an alternative to the coenzyme B12 dependent methylmalonyl-CoA pathway for propionate oxidation, is not used because it would interfere with the Krebs cycle and thereby compromise the high-energy requirement of the nervous system. In the diol dehydratases the 5'-deoxyadenosyl radical generated by homolysis of the carbon-cobalt bond of coenzyme B12 moves about 10 A away from the cobalt atom in cob(II)alamin. The substrate and product radicals are generated at a similar distance from cob(II)alamin, which acts solely as spectator of the catalysis. In glutamate and methylmalonyl-CoA mutases the 5'-deoxyadenosyl radical remains within 3-4 A of the cobalt atom, with the substrate and product radicals approximately 3 A further away. It is suggested that cob(II)alamin acts as a conductor by stabilising both the 5'-deoxyadenosyl radical and the product-related methylene radicals.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cobamides / chemistry*
  • Humans
  • Intramolecular Transferases / chemistry*
  • Methane / chemistry*
  • Substrate Specificity
  • Vitamin B 12 / analogs & derivatives*
  • Vitamin B 12 / chemistry

Substances

  • Cobamides
  • cob(II)alamin
  • Intramolecular Transferases
  • cobamamide
  • Methane
  • Vitamin B 12