Carbocyclic analogues of D-ribose-5-phosphate: Synthesis and behavior with 5-phosphoribosyl α-1-pyrophosphate synthetases

Article abstract of DOI:10.1016/0968-0896(96)00090-9

The synthesis of cyclopentyl and cyclopentenyl analogues of the α- anomer of D-ribose-5-phosphate from D-ribonolactone and D-ribose is described. These analogues, which have the same absolute configuration as D- ribose-5-phosphate, were incubated with PRPP synthetases in an attempt to prepare the corresponding carbocyclic PRPP analogues. The carbocyclic ribose- 5-phosphate analogues were found to be inhibitors, rather than substrates, for 5-phosphoribosyl α-1-pyrophosphate synthetases of both bacterial and human origin. The inhibitory behavior of the analogues is described.