Boc‐Protection on L‐DOPA: an Easy Way to Promote Underwater Adhesion. Issue 46 (13th November 2020)

• Record Type: Journal Article
• Authors: Giuri, Demetra; Jacob, Kiran A.; Ravarino, Paolo; Tomasini, Claudia
• Is Part Of: European journal of organic chemistry. Issue 46(2020)
• Page Start: 7144
• Page End: 7150
• Publication Date: 2020-11-13
• Subjects: Contact angles -- L‐DOPA -- Tack tests -- Traction tests -- Underwater adhesion; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202001264
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : The ability of mussels to adhere to underwater surfaces has attracted a lot of attention from the scientific community. As proteins containing L‐DOPA (3, 4‐dihydroxyphenyl‐l ‐alanine) are involved in their adhesion, a common strategy to synthesize adhesives is the incorporation of this amino acid into other compounds. Herein, we report a study on four compounds of the family of Boc x ‐(L‐DOPA) n ‐OMe ( x = 1–3; n = 1, 2), that we prepared through simple synthetic steps. Three of them showed the capability of underwater adhesion: while they are not adhesive in the dry phase, the adhesiveness is triggered when the dried sample is immersed in water or any aqueous solutions. The introduction of protecting groups stabilizes L‐DOPA, preventing the oxidation of the catechol moiety, and enhances the hydrophobicity, helping the removal of water from the surface to bind. These molecules show good adhesiveness, with different properties, so they may be all used as adhesives for different purposes. These outcomes pave the way for new applications for these materials as green and biocompatible adhesives. Abstract : Among four compounds of the family Boc x ‐(L‐DOPA) n ‐OMe ( x = 1–3; n = 1, 2), three of them show good adhesiveness. The introduction of protecting groups stabilizes L‐DOPA, preventing the oxidation of the catechol moiety and enhances the hydrophobicity. These materials show good adhesiveness, with different properties, so they may find applications as green and biocompatible adhesives.