Toward Non-Toxic Antifouling:Synthesis of Hydroxy-,Cinnamic Acid-,Sulfate-,and Zosteric Acid-Labeled Poly[3-hydroxyalkanoates]

摘要

The side-chain double bonds of bacterial poly[3-hydroxyalkanoate-co-3-hydroxyalkenoate](PHAE,1)were transformed into thioether bonds(derivative 2)via the radical addition reaction of 11-mercapto-l-undecanol.The terminal hydroxy functionalities of derivative 2 were subsequently esterified with cinnamic acid(derivative 3),sulfatized with C1SO_3H(derivative 4),or coupled with tert-butyldimethylsilyl-protected coumaric acid,to give,after deprotection with tetrabutylammonium fluoride(derivative 5)followed by sulfatization,p-(sulfooxy)cinnamic acid-(zosteric acid)labeled PHAE(derivative 6).The reactions proceeded with good yields and little side reactions,which was confirmed with ~1H NMR and GPC experiments.These functionalized polyesters are currently investigated as environmentally friendly coatings to protect surfaces from biofouling.