Ring contraction of hydroporphinoid to corrinoid complexes.
- Rasetti V Laboratory of Organic Chemistry, Eidgenössische Technische Hochschule Zürich, Universitätstrasse 16, CH-8092 Zürich, Switzerland.
- Pfaltz A
- Kratky C
- Eschenmoser A
- 1981-01-01
Published in:
- Proceedings of the National Academy of Sciences of the United States of America. - 1981
English
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.
- Language
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- English
- Open access status
- bronze
- Identifiers
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- DOI 10.1073/pnas.78.1.16
- PMID 16592942
- Persistent URL
- https://sonar.ch/global/documents/154255
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