Ring contraction of hydroporphinoid to corrinoid complexes
- 1 January 1981
- journal article
- Published by Proceedings of the National Academy of Sciences in Proceedings of the National Academy of Sciences
- Vol. 78 (1) , 16-19
- https://doi.org/10.1073/pnas.78.1.16
Abstract
Crystalline nickel(II) and dicyanocobalt(III) complexes of a racemic 1,2,2,7,7,12,12,17,17,20-decamethyl-20-hydroxy-1,2,3,7,8,12,13,20-octahydro- 17H-porphyrin rearrange to the corresponding complexes of racemic 19-acetyl-1,2,2,7,7,12,12,17,17-nonamethyl-trans-corrin on melting (approximately 290 degrees C and 260 degrees C, respectively). The nickel(II) 19-acetylcorrinate formed in this way is shown to deacetylate to racemic nickel(II) 1,2,2,7,7,12,12,17,17-nonamethyl-trans-corrinate on treatment with 2 M KOH. These reactions are being studied as potentially biomimetic chemical models for the elusive ring contraction step in vitamin B(12) biosynthesis.Keywords
This publication has 3 references indexed in Scilit:
- Biosynthesis of vitamin B12: mode of incorporation of factor III into cobyrinic acid.Proceedings of the National Academy of Sciences, 1981
- Biosynthesis of vitamin B12: identity of fragment extruded during ring contraction to the corrin macrocycle.Proceedings of the National Academy of Sciences, 1981
- Biosynthesis of vitamin B12: nature of the volatile fragment generated during formation of the corrin ring system.Proceedings of the National Academy of Sciences, 1981