Compositions and methods for sulfation of carbohydrates
AssigneeThe Trustees of Boston College
InventorsJia Niu, Chao Liu, Cangjie Yang
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AssigneeThe Trustees of Boston College
InventorsJia Niu, Chao Liu, Cangjie Yang
Estimating the term…
In one aspect, the disclosure relates to a facile strategy to introduce electron-deficient aryl sulfate diesters to silylated hydroxyl groups of carbohydrates and amino acids, among other substrates, wherein selective hydrolysis and the removal of an electron-deficient aromatic group allows for the efficient generation of sulfated carbohydrates, peptides, and other compounds. The incorporation of electron-deficient aryl sulfate diesters in the early stage of the synthesis of glycans, peptides, and the like, disclosed herein avoids time-consuming protecting group manipulations, simplifies the purification of sulfated products, and improves the overall yield and efficiency. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present disclosure.
A method for synthesis of masked sulfate diesters, the method comprising contacting a substrate having at least one hydroxyl group with an aryl fluorosulfate, a silylating reagent, and a base catalyst in a solvent to produce a product sulfate diester, and wherein the substrate comprises a sugar, a sugar comprising at least one protected hydroxyl group, a polysaccharide, a glycosaminoglycan, or a combination thereof.
Dependencies are inferred from the claim text.