Synthesis and Characterization of Highly Thiolated Silk Fibroin

Abstract

AbstractCovalent attachment of thiols to the tyrosine residues of silk fibroin is accomplished with a high degree of functionalization through the reaction of a pyridyldithiol‐containing N‐hydroxysuccinimidal‐ester and an amino‐tyrosine silk intermediate. The extent of thiol modification is characterized by 1H NMR and UV–vis spectroscopy. Further modification of the thiol groups is probed by reacting with an iodoacetamide‐containing small molecule resulting in a novel fluorescent silk derivative. Last, the ability of the thiolated silk to form hydrogels in situ is investigated.