94(P-24) Syntheses of Functional Cellulose : Introduction of a Linker Containing an Imidoyl Ester Group into Several Carbohydrate Derivatives
Details
Covalent attachment of small molecules to proteins has been a target of numerous synthetic endeavors because this process covers nonimmunogenetic molecules into immonogenetic materials. The application of this concept to carbohydrates provided the foundation to generate anti-oligosaccharide antibodies. Active ester linkers such as the readily available DSG, MBS and the synthesized maleimide bifunctional linkers have become very useful in the area of bioconjugate chemistry. These linkers allow the conjugation of amino group containing molecules such as peptides having amino acid residues and protein. This allows the construction of various moieties including protein-conjugate haptens, immobilized antibodies or enzymes, immuno-conjugates or -toxins, and immunodiagnostic agents. Here, we describe a new approach to biocojugation utilizing the active ester linker containing acid chloride 1 and 2 that may take place the acylation. Although the active ester method has been studied in carbohydrate field, this linker has not previously been used for bioconjugation saccharides. The active ester linkers 1 and 2 are obtained from the carboxyl dichloride and N-hydroxyphthalimide in one step. N-hydroxyphthalimide gives 1 and 2 (34 and 44%) by succinyl chloride and glutaryl chloride in the presence of pyridine. We introduced active ester linkers into a modified glucose by two kinds of path. One is of using DCC to introduce active ester linker into 6-OH of modified glucose by two steps. Another is of using acid chloride linker containing acid chloride into 4,6-OH modified glucose with pyridine by one step. Furthermore, we tried to introduce the linker into cellulose by one step.
