3 years ago

Alpha- and Beta-Diastereoisomers of Phenylcobalamin from Cobalt-Arylation with Diphenyliodonium Chloride

Alpha- and Beta-Diastereoisomers of Phenylcobalamin from Cobalt-Arylation with Diphenyliodonium Chloride
Bernhard Kräutler, Markus Ruetz, Christopher Brenig, Klaus Wurst, Christoph Kieninger
Organometallic aryl-cobalamins are B12-derivatives featuring properties of potential ‘B12 antivitamins’. Herein, we describe a new method for the preparation of aryl-cobalamins using versatile diaryliodonium salts as arylation agents. Formate or sodium borohydride reduction of aquocobalamin in presence of diphenyliodonium chloride furnished Coβ-phenyl-cobalamin PhCbl in a roughly 3:1 to 1:1 ratio with its coordination isomer αPhCbl, a first representative ‘base-off’ Coα-aryl-cobalamin. The new structures were secured by detailed spectroscopic analysis, supplemented by an X-ray crystal structure analysis of PhCbl. Both types of coordination isomers of the aryl-cobalamins promise to be useful molecular tools in biomedical and biological studies. Up or down? That is the question: A new method of cobalt-arylation of vitamin B12-derivatives produces βPhCbl and αPhCbl, both possible coordination isomers of phenylcobalamin. Such arylcobalamins may function as ‘B12 antivitamins’ and help decipher new pathways and mechanisms of B12-dependent metabolism.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201701514

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