| Toward non-toxic antifouling: synthesis of hydroxy-, cinnamic acid-, sulfate-, and zosteric acid-labeled poly[3-hydroxyalkanoates]. | |
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MedLine Citation:
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PMID: 15244464 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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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. |
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Authors:
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Roland Hany; Christine Böhlen; Thomas Geiger; Manfred Schmid; Manfred Zinn |
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Publication Detail:
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Type: Journal Article |
Journal Detail:
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Title: Biomacromolecules Volume: 5 ISSN: 1525-7797 ISO Abbreviation: Biomacromolecules Publication Date: 2004 Jul-Aug |
Date Detail:
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Created Date: 2004-07-12 Completed Date: 2005-02-09 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 100892849 Medline TA: Biomacromolecules Country: United States |
Other Details:
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Languages: eng Pagination: 1452-6 Citation Subset: IM |
Affiliation:
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Swiss Federal Laboratories for Materials Testing and Research (EMPA), CH-8600 Dübendorf, Switzerland. roland.hany@empa.ch |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Acids
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chemistry* Biofilms / drug effects Cinnamates / chemistry Hydroxy Acids / chemistry Molecular Structure Polyesters / chemical synthesis*, metabolism*, toxicity Pseudomonas putida / chemistry Sulfates / chemistry Toxicity Tests |
| Chemical | |
Reg. No./Substance:
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0/Acids; 0/Cinnamates; 0/Hydroxy Acids; 0/Polyesters; 0/Sulfates; 621-82-9/cinnamic acid |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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