A new general method to covalently link a peptide to cotton via thiazolidine ring formation is developed. Three different analogues of an ultrashort antibacterial peptide are synthesized to create an antibacterial fabric. The chemical ligation approach to the heterogeneous phase made up of insoluble cellulose fibers and a peptide solution in water is adapted. The selective click reaction occurs between an N-terminal cysteine on the peptide and an aldehyde on the cotton matrix. The aldehyde is generated on the primary alcohol of glucose by means of the enzyme laccase and the cocatalyst 2,2,6,6-tetramethylpiperidine-1-oxyl. This keeps the pyranose rings intact and may bring a benefit to the mechanical properties of the fabric. The presence of the peptide on cotton is demonstrated through instant colorimetric tests, UV spectroscopy, IR spectroscopy, and X-ray photoelectron spectroscopy analysis. The antibacterial activity of the peptides is maintained even after their covalent attachment to cotton fibers.
