Preparation and uses of locked-ring sugar C-glycoside derivatives
AssigneeThe United States of America as represented by the Secretary of Agriculture
InventorNeil P. Price
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Abstract
“Locked-ring” C-glycoside derivatives may be prepared wherein the ring of the sugar molecule remains intact without the need for any protecting groups. These C-glycoside derivatives may be produced by first reacting an aldose reducing sugar, which may be a hexose or a pentose, with a β-diketone to form a C-glycoside ketone. The C-glycoside ketone is then reacted with a ketone reactive compound, such as a hydrazine or hydroxylamine, optionally linked to a detectable label, to form a C-glycoside derivative wherein the ketone reactive compound is conjugated to the C-glycoside at the site of the ketone. The aldose reducing sugar used in the first reaction may a simple pentose or hexose monosaccharide, or it may be optionally substituted.
Claims13
A method for preparing sugar C-glycoside derivatives comprising:
- a) reacting an aldose reducing sugar with a β-diketone under conditions and for a period of time effective to form a C-glycoside ketone, which said aldose reducing sugar comprises an aldehyde containing hexose aldose reducing sugar or an aldehyde containing pentose aldose reducing sugar, wherein said hexose is optionally substituted at one or more of the C2, C3, C4, C5, and C6 positions thereof and said pentose is optionally substituted at one or more of the C2, C3, C4, and C5 positions thereof, and
- b) reacting said C-glycoside ketone with a ketone reactive compound, which said ketone reactive compound is optionally linked to a detectable label or solid surface, under conditions and for a period of time effective to form a C-glycoside derivative wherein said ketone reactive compound is conjugated at the carbon of the ketone of said C-glycoside ketone, and the ring structure of said sugar remains intact,
- wherein said ketone reactive compound is selected from the group consisting of hydrazines or hydrazides, semicarbazides, and thiols, and said C-glycoside derivative is selected from the group consisting of C-glycoside ketohydrazones, C-glycoside semicarbazones, and C-glycoside thiolketones, respectively.
Dependencies are inferred from the claim text.