Toward non-toxic antifouling: synthesis of hydroxy-, cinnamic acid-, sulfate-, and zosteric acid-labeled poly[3-hydroxyalkanoates].
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-1-undecanol. The terminal hydroxy functionalities of derivative 2 were subsequently esterified with cinnamic acid (derivative 3), sulfatized with ClSO(3)H (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 (1)H NMR and GPC experiments. These functionalized polyesters are currently investigated as environmentally friendly coatings to protect surfaces from biofouling.
Hany
Roland
R
Swiss Federal Laboratories for Materials Testing and Research (EMPA), CH-8600 Dübendorf, Switzerland. roland.hany@empa.ch
Böhlen
Christine
C
Geiger
Thomas
T
Schmid
Manfred
M
Zinn
Manfred
M
D000143:Acids / Q000737:chemistry*; D018441:Biofilms / Q000187:drug effects; D002934:Cinnamates / Q000737:chemistry; D006880:Hydroxy Acids / Q000737:chemistry; D015394:Molecular Structure; D011091:Polyesters / Q000138:chemical synthesis* / Q000378:metabolism* / Q000633:toxicity; D016958:Pseudomonas putida / Q000737:chemistry; D013431:Sulfates / Q000737:chemistry; D018675:Toxicity Tests
D000143:Acids; D002934:Cinnamates; D006880:Hydroxy Acids; D011091:Polyesters; D013431:Sulfates; C029010:cinnamic acid