SYNTHESIS OF A NEW SPIRONUCLEOSIDE: SULFAHYDANTOCIDINE

The chemistry of spironucleosides, a type of nucleoside in which the anomeric carbon belongs simultaneously to the sugar ring and to the nitrogenated heterocyclic moiety, has received a considerable development in the last... [ view full abstract ]

The chemistry of spironucleosides, a type of nucleoside in which the anomeric carbon belongs simultaneously to the sugar ring and to the nitrogenated heterocyclic moiety, has received a considerable development in the last decade especially from the isolation of (+)-hydantocidin , the first natural spironucleoside1, which shows low toxicity for mammals and has herbicidal and plant growth-regulatory activities2. Glucopyranose  analogue of hydantocidin was discovered in 1995 has a significant inhibition for glycogen phosphorylase3, an enzyme that catalyzes the regulation of glycogen degradation.

In this communication, we report the preparation of new spironucleoside the Sulfahydantocidine, starting from the D (+)-Ribolactone, using chlorosulfonylisocyanate to incorporate the sulfamoyl moiety.

1- Haruyama, H.; Takayanna, T.; Kinosita, T.; Kondo, M.; Nakajima, M.; Haneishi, T. J.Chem. Soc. Perkin Trans. 1, 1991, 1637-1640.

2- Poland, B. W.; Lee, S. F.; Subramanian, M. V.; Siehl, D. L.; Andersen, R. J.; Fromm, H .J.; Honzatko, R. B. Biochemistry 1996, 35, 15753-15759.

3- Gyémant, G.; Kandra, L.; Nagy, V.; Somsak, L. Biochem. Biophys. Res. Commun. 2003, 313, 334-339.