C-Linked Glycosides: Towards The Synthesis of C-Spoxazomicin C-Linked Glucoside

Additional Funding Sources

This research was supported by the University of Idaho.

Presentation Date

7-2018

Abstract

Gylcosides have been shown to be more biologically active than a molecule lacking a glycosidic bond. By swapping out the oxygen linkage of the sugar with a carbon linkage, it has been shown to have a larger half life. Spoxazomicin-C (1) is a molecule found in Streptomyces sp. RM-14-6. (1) is the aglycone, it showed markedly less neuroprotective activity when introduce to ethanol toxicity in comparison to the glycoside (2). I have been trying to synthetically Produce (2) from phthalide linking it with the amino acid with L-serine followed with a condensation to create a oxazolidne structure than creating a carbon linkage with a sugar.

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C-Linked Glycosides: Towards The Synthesis of C-Spoxazomicin C-Linked Glucoside

Gylcosides have been shown to be more biologically active than a molecule lacking a glycosidic bond. By swapping out the oxygen linkage of the sugar with a carbon linkage, it has been shown to have a larger half life. Spoxazomicin-C (1) is a molecule found in Streptomyces sp. RM-14-6. (1) is the aglycone, it showed markedly less neuroprotective activity when introduce to ethanol toxicity in comparison to the glycoside (2). I have been trying to synthetically Produce (2) from phthalide linking it with the amino acid with L-serine followed with a condensation to create a oxazolidne structure than creating a carbon linkage with a sugar.