Toward non-toxic antifouling: synthesis of hydroxy-, cinnamic acid-, sulfate-, and zosteric acid-labeled poly[3-hydroxyalkanoates].

Biomacromolecules
Roland HanyManfred Zinn

Abstract

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.

References

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Citations

Jul 14, 2011·Langmuir : the ACS Journal of Surfaces and Colloids·Agnieszka JagodaKatarzyna Kita-Tokarczyk
Nov 18, 2010·Natural Product Reports·Nobuhiro Fusetani
May 18, 2016·New Biotechnology·Martin KollerGerhart Braunegg
Feb 9, 2017·Langmuir : the ACS Journal of Surfaces and Colloids·Antoine VenaultYung Chang
Jul 18, 2018·Critical Reviews in Microbiology·Cristina CattòFrancesca Cappitelli
May 29, 2015·Bioengineering·Martin Koller, Gerhart Braunegg
May 17, 2019·Biomacromolecules·Xu ZhangGuo-Qiang Chen
Feb 13, 2007·Biomacromolecules·Manfred SchmidManfred Zinn

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