The shikimate pathway. Part IV. The stereochemistry of the 3-dehydroquinate dehydratase reaction and observations on 3-dehydroquinate synthetase

Abstract

The conversion of 3-dehydroquinate (1,3,4-trihydroxy-5-oxocyclohexanecarboxylate)(8) into 3-dehydroshikimate (4,5-dihydroxy-3-oxocyclohex-1-enecarboxylate)(9) involves the syn-elimination of the elements of water; this observation confirms earlier work on the reaction. Studies on the 3-dehydroquinate synthetase reaction show it to possess a stereospecificity with respect to the C-7 protons of the substrate 3-deoxy-D-arabino-heptulosonic acid 7-phosphate (7).