Model studies for the thiol-mediated methyl transfer to corrinoids
| Autor: | Tamis Darbre, Christina Wedemeyer-Exl, Reinhart Keese |
|---|---|
| Rok vydání: | 2007 |
| Předmět: |
Alkylation
Stereochemistry Buffers Methylation Biochemistry Medicinal chemistry Methylating Agent chemistry.chemical_compound Phenols Oximes Pyridine Reactivity (chemistry) Sulfhydryl Compounds Physical and Theoretical Chemistry Corrinoids chemistry.chemical_classification Molecular Structure Chemistry Spectrum Analysis Organic Chemistry Glutathione Solutions Hexane Models Chemical Thiol Methyl iodide |
| Zdroj: | Organic & Biomolecular Chemistry. 5:2119 |
| ISSN: | 1477-0539 1477-0520 |
| DOI: | 10.1039/b703421k |
| Popis: | The thiol-dependent methylation of heptamethyl cob(II)yrinate 8r with methyl iodide and methyl tosylate was explored under a variety of conditions. The interaction of the heptamethyl cob(II)yrinate with a variety of thiols was monitored prior to the addition of the methylating agent, and the formation of the Co(I) complex was only apparent in the reaction with hexane thiol. Nevertheless, thiol-mediated methylation of the Co(II) complex 8r takes place with methyl iodide under most conditions. The Co-methylation with methyl tosylate showed a different reactivity, was inhibited by pyridine or N-methylimidazole, and was strongly dependent on the the acidity of the thiol used. Mechanistic aspects are discussed. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|