Stereochemistry of the enzymatic and non-enzymatic conversion of 3-dehydroshikimate into protocatechuate

Abstract

Using substrate tritiated stereospecifically at C-6 it was shown that the dehydroshikimate dehydratase reaction involves the syn-elimination of the elements of water, whereas the acid-catalysed chemical conversion of 3-dehydroshikimate into protocatechuate proceeds non-stereospecifically and involves a hydrogen isotope effect.