Carbocyclic analogues of D-ribose-5-phosphate: synthesis and behavior with 5-phosphoribosyl alpha-1-pyrophosphate synthetases.
The synthesis of cyclopentyl and cyclopentenyl analogues of the alpha-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 alpha-1-pyrophosphate synthetases of both bacterial and human origin. The inhibitory behaviour of the analogues is described.
Parry
R J
RJ
Department of Chemistry, Rice University, Houston, Texas 77251, USA.
Burns
M R
MR
Skae
P N
PN
Hoyt
J C
JC
Pal
B
B
D006801:Humans; D006863:Hydrogen-Ion Concentration; D007700:Kinetics; D011742:Pyrimidine Nucleotides / Q000378:metabolism; D012268:Ribose-Phosphate Pyrophosphokinase / Q000378:metabolism*; D012267:Ribosemonophosphates / Q000138:chemical synthesis* / Q000378:metabolism; D012486:Salmonella typhimurium; D013237:Stereoisomerism
D011742:Pyrimidine Nucleotides; D012267:Ribosemonophosphates; C082815:4-amino-8-(ribofuranosylamino)pyrimido(5,4-d)pyrimidine-5'-phosphate; C031626:ribose-5-phosphate; D012268:Ribose-Phosphate Pyrophosphokinase