Carbocyclic analogues of d-ribose-5-phosphate: Synthesis and behavior with 5-phosphoribosyl α-1-pyrophosphate synthetases Original Research Article

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.