A Polyhydroxylated Cyclopentene: A Useful Synthon toward the Synthesis of Carbocyclic D-Fructofuranoid

نویسندگان

  • Mohindra Seepersaud
  • Richard Bucala
  • Yousef Al-Abed
چکیده

Fructose 2,6-bisphosphate (1) is formed by phosphorylation of fructose-6-phosphate, a key substrate in the glycolysis pathway, in a reaction catalyzed by phosphofructokinase-2 (PFK-2) [1]. Fructose-2,6-bisphosphate is a powerful allosteric regulator of glycolysis via its potent stimulatory effect on phosphofructokinase-1 activity and its in­ hibitory effect on fructose-1,6-bisphosphatase. The recent identification of an inducible isoform of PFK-2 that is specifically induced by inflammation stimuli or oncogenic transformation has suggested that fructose analogs might serve as useful phar­ macophores for inhibiting cell activation and can­ cer cell growth [2, 3]. Unlike phosphorylated fruc­ tose, carbocyclic D-fructofuranoside (2) (Fig. 1) can not be metabolized and therefore can be shut­ tled repeatedly through cycles of kinase and phos­ phatase activity. Wilcox and Guadino [4] have shown the first and only synthetic approach to carbocyclic D-fructofuranoside (3) (Scheme 1). The overall synthesis in­ volved 12 steps. Cyclopentane ring closure was accomplished utilizing a free-radical mediated

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تاریخ انتشار 1999