Starch and its derivatives have a myriad of biomedical and industrial applications due to their attractive physicochemical properties such as biodegradability and biocompatibility. In addition, they are, readily available, cheap to acquire and are chemically modifiable. The chemical versatility of starch allows for the synthesis of hybrid constructs with polymers and other biomolecules, such as protein and peptides, to be more accessible. Different functional groups such as aldehydes and alcohols on starch can be modified to other functional groups or used to covalently link other molecules. Selective modification of the reducing end of starch to an alkyne provides an orthogonal conjugation strategy through copper-catalyzed azide-alkyne cycloaddition or click chemistry. Our research group aims to synthesize and characterize a novel hybrid conjugate consisting of peptides, hetero-functionalized dibromomaleimide linker, and starch for peptide delivery. Attachment of a versatile small molecule linker such as, dibromomaleimide, to the reducing end of starch provides an attractive scaffold for the intracellular delivery of peptide therapeutics with increased stability. In this work, we show the optimal synthesis and characterization of starch functionalized with dibromomaleimide-based linker. Our prospective work also includes investigating optimal click reaction conditions to prepare the starch-linker complex and 19F NMR experiments to further analyze and confirm the synthesis of the starch conjugate. These well characterized constructs serve as precursor molecules for the preparation of hybrid starch-peptide bioconjugates for applications such as drug delivery.

Synthesis and characterization of starch-dibromomaleimide conjugates for delivery applications

256th National Meeting (2018)

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