Synthesis and Characterization of Water- Soluble Polymers with Pendant Nitrocatecholic Functionalities

摘要

The versatile chemistry of the modified, catecholic amino acid 3,4- dihydroxyphenylalanine (DOPA) is integral to the remarkable properties of the adhesive proteins of the mussel (Mytilus californianus, M. edulis) and sandcastle worm (Phragmatoma californica). Catecholic compounds are capable of robust, reversible chemisorption to metal oxide surfaces and strong complexation of free metal ions which play important roles in the function of the mussel byssus and sandcastle worm glue. A 2-electron oxidation of DOPA to the highly reactive DOPAquinone usually compromises metal complexation but can lead to the formation of diDOPA crosslinks, thought to contribute to cohesive strength in marine adhesives. This reaction can be triggered by mild oxidizing agents or through autoxidation, which proceeds rapidly at alkaline pH. Uncontrolled oxidation can lead to premature curing and loss of adhesive strength in isolated marine adhesive proteins or synthetic catecholic constructs.