Absolute configuration of (+)-5-(o-hydroxyphenyl)-5-phenylhydantoin, the major metabolite of 5,5-diphenylhydantoin in the dog.
5-(3-Hydroxyphenyl)-5-phenylhydantoin (m-HPPH) has been resolved by crystallization of the brucine salts. The (+) enantiomer has been converted to (-)-5-cyclohexyl-5-phenylhydantoin, a compound previously demonstrated to have the R configuration. The R configuration can accordingly be assigned to (+)-m-HPPH, the principal metabolite of 5,5-diphenylhydantoin (phenytoin) in the dog.
D003460:Crystallization; D006900:Hydroxylation; D008722:Methods; D008968:Molecular Conformation; D010672:Phenytoin / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000378:metabolism*; D013237:Stereoisomerism
D010672:Phenytoin