Adhesives, marine synthesis

Three novel related marine alkaloids, halichlorine (1148) from the sponge Halichondria okadai (1177, 1178) and pinnaic acid (1149) and tauropinnaic acid (1150) from the bivalve Pinna muricata (1179), have been the objects of much synthetic interest in view of their pronounced biological activity (inhibition of the vascular cell adhesion molecule-1) (1180). Synthesis of these alkaloids led to both revision and confirmation of the original structures (1181,1182). The syntheses of the previously known chlorine-containing cylindricines have been reviewed (1183). 

Bacterial Polysaccharides. Many bacterial species release exopolysaccharides into their environment. The synthesis of capsular and slime polysaccharides or similar sticky surface materials serves as an adhesive to attach the bacteria to solid substrates, even in a marine environment. These polysaccharides range from compositionally simple homopolymers to very complex heteropolymers composed of several individual sugars linked in a variety of ways. 

Uses Monomer for creating and modifying polymers, acrylic resins, urethane methacryiates marine antifouling paint resin comonomer reactive comonomer for acryiic and S/B resins rubber modifier binder for textiies/paper adhesives, nonwoven fabrics, enamels, adhesives grafting of textiie fibers scaie inhibitors adhesion promoter for polymers hydrophilic polymers It.-curing polymer systems reactive thinner for radiation curing food-pkg. adhesives, polymers Manuf./Distrib. Acros Org. Aldrich Allchem Ind. Ashland BP Amoco Electron Microscopy Sciences Fluka ICN Biomed. Research Prods. Kessler Lancaster Synthesis Laporte Perf. Chems. Monomer-Polymer Dajac Labs Pfaltz Bauer Rohm Haas Rohm Tech San Esters Scientific Polymer Prods. Sigma TCI Am. Ubichem pic Whyte Chems. Ltd... 

Scheme 2 Catechol monomers and initiators used in synthesis of polymer mimics of marine adhesive proteins.

Synthetic chemistry has progressed by leaps and bounds in recent decades, especially with regard to the ability to make peptides and even small proteins. In the case of marine adhesive proteins, however, total synthesis is not terribly practical. Some of the adhesive proteins have molecular weights upward of 100,000 mass units, which is currently inaccessible to fully synthetic proteins. Even when small proteins are synthesized, only very small quantities can be obtained, and at great cost. 

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