We recently reported the complete dissolution of tetrabutylammonium salts of alginates in dipolar aprotic solvents containing tetrabutylammonium fluoride. Acylation of the alginate hydroxyl groups in these solvent systems was described, yielding water soluble derivatives. The synthesis of organo-soluble alginate derivatives requires modification of the carboxylate groups using reagents which impart sufficient hydrophobicity to the alginate backbone. The dissolution of alginates in non-aqueous media allows the use of hydrophobic organic reagents, difficult or impossible to use in aqueous solvents. We therefore report on the synthesis of alginate esters using SN2 chemistry to generate fully or partially substituted benzyl, butyl, ethyl and methyl derivatives. These new products possess the potential to be drug carriers themselves, or act as intermediates in the synthesis of further derivatized alginate drug delivery systems. The method is also a promising route to covalently attach drugs or bio-functional molecules to the alginate backbone, with high degrees of substitution.

Synthesis of organo-soluble alginate esters via carboxyl group modification

243rd National Meeting (2012)

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