Synthesis Nitrophenol Resins

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Overview Solid phase reagent chemistry has received a lot of attention as an alternative approach to conventional solid phase combinatorial synthesis. Whereas the solid phase method involves the solid support on which the growing compound is loaded, modified and later cleaved from, solid phase reagent method involves the addition of the solid phase reagents to the library molecule residing in solution. After the synthesis is complete, the solid phase reagents are then removed from the reaction mixture by filtration. In particular, polymeric ester reagents are known useful tools for amide/sulfonamide library synthesis and for labelling biologically important amines and proteins. Most of the reported functionalities, including nitrophenol, have been attached to resin solid support by method limiting the selection of resin compositions to those with poor swelling properties in hydrophilic solvents and thus restricting reaction conditions to hydrophobic organic solvents. Dr. Chang and co-workers have found a way to circumvent the above-described limitations by devising a novel method of synthesis of nitrophenol resins that allows for selecting from wide variety of resin compositions that can be used for synthesis in most organic solvents and also aqueous media. Project Description Dr. Chang and co-workers claim two novel methods of nitrophenol resin synthesis. One method involves amide bond formation between commercially available hydroxyl nitro benzoic acid and amino-alkyl polymer support, such as polystyrene (PS), TentaGel (TG), PEGA, macroporous (MP) resin and silica gel (SG), using DIC-HOBt coupling. The other method utilizes hydrolysis of chlorobenzene. The production expenses of these methods are much lower than for comparable tetrafluorophenol resins. The authors further showed that the newly synthesized nitrophenol resins could be used as reactive acylating and sulfonylating reagents for production of highly pure amide and sulfonamide libraries. Importantly, water compatible property of TG, PEGA and SG resin allows the amination reaction to proceed in aqueous media. Applications: The resins of the present invention can be used as tools for synthesis of arrays of highly pure amide and sulfonamide libraries. These resins can also be used as labelling reagents for biologically important amines and proteins in various conditions including aqueous media, which is important in the field of proteomics. Patent Status: U.S. patent application have been filed covering this novel technology