Synthesis of (+)-(1S)-1-pyrophosphoryl-(2R, 3R)-2,3-dihydroxy-(4S)-4-(phosphoryloxymethyl)cyclopentane, a stable, optically-active carbocyclic analog of 5-phosphoribosyl-1-pyrophosphate (PRPP)

Article abstract of DOI:10.1016/S0040-4020(97)00387-6

A total synthesis of the cyclopentyl analog of the important biochemical intermediate 5-phosphoribosyl-1-pyrophosphate (PRPP) is reported. The synthesis proceeds from the benzylidene acetal of D-ribonolactone to the correct enantiomeric form of the cyclopentyl PRPP analog in ca. 4% overall yield. Because of the low reactivity of the carbocyclic analog compared to PRPP, the compound should be a highly useful tool for mechanistic and crystallographic investigations of the phosphoribosyltransferases, a family of enzymes that utilizes PRPP as a substrate.