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Sandra's Project Page - CAMP Summer 2007 |
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Intern: Sandra Bravo, Biology
Mentor: Abdul Hackim
Faculty Supervisor: Daniel Little
Department: Chemistry and Biochemistry |
FORMATION OF A-C-GLYCOSIDE
Glycoside linkages are significant elements of numerous bioactive natural
products. Numerous antibiotics and anticancer agents contain a sugar group
attached to an aglycone through a standard O-linked glycoside bond. Although
there are various cases of C-linked glycosides, they are less well-known. The
C-glycoside is more stable compared to the O-glycoside linkages which are
susceptible to chemical or enzymatic cleavage. This raises the idea of possibly
replacing relatively unstable O-glycosidic linkages of natural products with
more stable C-glycosidic linkages. However, the bioactivity of such molecules
may be affected, due to the different geometries resulting from a carbon linked
glycoside versus an oxygen linked glycoside. To be able to understand the effect
of replacing the O-glycoside bond, the focus of this research is to investigate
the creation of a C-glycoside. The following is one of several existing methods
for the formation of an ?-C-glycoside which is used for this research. The
first step is creating an epoxide which is then opened with the addition of
titanocene dichloride. The resulting radical is trapped by a stabilizing group
which in this case is phenyl vinyl sulfone. The resulting molecule can then
undergo a Julia olefination reaction allows broadening the utility of the
C-glycoside. The expected result is to accomplish the reactions and expect the
replacement of an O-glycosidic bond with a C-glycosidic bond to increase
stability and decrease enzyme/chemical cleavages.
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