The complete stereochemistry of the enzymatic dehydration of 4-hydroxybutyryl coenzyme A to crotonyl coenzyme A

Article abstract of DOI:10.1002/anie.200705473

(Chemical Equation Presented) The stereospecific action of the microbial enzyme 4-hydroxybutyryl-CoA dehydratase on the three prochiral centers of its substrate 4-hydroxybutyryl-CoA can now be described as anti elimination of the 2Re and 3Si hydrogen atoms with retention of configuration during the substitution of the hydroxy group by a hydrogen atom. The results confirm the relationship of the dehydratase to acyl-CoA dehydrogenases and the view that the Fe₄S₄ cluster acts as a Lewis acid.