Available at: http://digitalcommons.calpoly.edu/theses/972
Date of Award
MS in Polymers and Coatings
Chemistry & Biochemistry
Philip J. Costanzo
One less commonly used “click” reaction is thiazolidine chemistry. Thiazolidine chemistry is a commonly used reaction used in biological systems because the reaction requires the presence of both cysteine (a common amino acid) and an aldehyde or ketone. If cysteine residues could be incorporated into a polymer then a variety of applications could be developed. Polymers containing free thiols (aka thiomers) have developed in the last decade to become great mucoadhesives. If there was a facile route to control the amount of free thiols along the polymer then more fine-tuned and potentially stronger adhesives could be made. For these reasons the attachment of cysteine residues in a facile way via reversible addition fragmentation chain transfer (RAFT) polymerization or small molecule synthesis was researched. The incorporation of latent cysteine residues into the polymer via post polymerization modification proved to be less successful. However protected cysteine molecules have been successfully ligated onto polymerizable monomers and have been show to be easily deprotected in the presence of an acid source.