Orthogonal Modification of Biopolymers with Variable Peptide Sequences via Ultra-Rapid Covalent Modification

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In the present proposal, ultra-rapid ambient temperature and catalyst-free coupling chemistry is investigated to be employed to bind monomer sequence-defined peptides onto biopolymer based surfaces. The aim will be to ultimately develop an access route to peptide modified biosubstrates, where the peptide segments constitute functions such as specific cell adhesion, biocidal activity or modulation of crystallization processes. The current proposal will demonstrate that extremely mild and catalyst-free conjugation strategies are ideally suited to ligate sensitive biomolecules to biological substrates.The overall aim of the project is subdivided into individual work packages, which have well-defined aims of their own. These are (i) the pre-functionalization and characterization of variable poly(saccharide) surfaces, e.g. cellulose, chitin, chitosan and hyaluronic acid systems, with highly electron deficient dithioesters, (ii) the establishment of a synthetic methodology to introduce dithioester or cyclopentadienyl moieties to supported peptides including model studies of the coupling of these in homogenous solution to synthetic polymers or soluble poly(saccharides), (iii) the functionalization of the electron deficient dithioester decorated poly(saccharide) surfaces with peptide sequences as well as the in-depth characterization of the generated surfaces, and (iv) the application of the developed ultra-rapid ambient temperature grafting procedure for the preparation of functional substrates.