Structural Chemistry

Proceedings of the Indian Academy of Sciences - Chemical Sciences

, Volume 93, Issue 3, pp 261-269

Structures of isopropylidene nucleoside derivatives: implications for ribose ring flexibility under external cyclic constraints

  • M. A. ViswamitraAffiliated withDepartment of Physics and ICMR Centre on Genetics and Cell Biology, Indian Institute of Science
  • , N. GauthamAffiliated withDepartment of Physics and ICMR Centre on Genetics and Cell Biology, Indian Institute of Science

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Abstract

Crystal structures of six isopropylidene nucleoside derivatives are described. The results show that, under external cyclic constraints, the ribose assumes a variety of unusual conformations. In those compounds which possess a base-to-sugar cyclization through the C(4′) atom, the furanose pucker is predominantly C(4′)-endo, O(4′)-exo. The possible relevance of the sulphur geometry in two of the compounds to certain structural aspects of the action of the enzyme thymidylate synthetase is also pointed out.

Keywords

Crystal structure isopropylidene nucleoside derivatives ribose ring flexibility sulphur geometry external cyclization