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. 1981 Jan;78(1):16-9.
doi: 10.1073/pnas.78.1.16.

Ring contraction of hydroporphinoid to corrinoid complexes

V Rasetti  1 , A Pfaltz, C Kratky, A Eschenmoser
Affiliations

Ring contraction of hydroporphinoid to corrinoid complexes

V Rasetti et al. Proc Natl Acad Sci U S A. 1981 Jan.

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.

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References

    1. Proc Natl Acad Sci U S A. 1981 Jan;78(1):9-10 - PubMed
    1. Proc Natl Acad Sci U S A. 1981 Jan;78(1):13-5 - PubMed
    1. Proc Natl Acad Sci U S A. 1981 Jan;78(1):11-2 - PubMed

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