Regioelectronic factors in metabolic hydroxylation of aliphatic carbon atoms |
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Authors: | Bernard Testa Jean-Claude Bünzli William P Purcell |
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Institution: | University of Lausanne, Switzerland |
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Abstract: | EHT calculations have been performed on model molecules acting as substrates for mammalian mono-oxygenases. Cα---H bonds are consistently found to have larger overlap populations compared with Cβ---H and Cγ---H bonds. It is known on the other hand that metabolic hydroxylation of aliphatic carbon atoms shows a marked regioselectivity for α-carbons. The quantum-mechanical results sustain the view that C---H bonds of relatively high electronic density are preferred target sites for the cytochrome P-450-mediated oxygenation, and that the oxygen atom being activated is transformed into an electrophilic species capable of C---H bond insertion. |
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