Document Detail

Toward non-toxic antifouling: synthesis of hydroxy-, cinnamic acid-, sulfate-, and zosteric acid-labeled poly[3-hydroxyalkanoates].
MedLine Citation:
PMID:  15244464     Owner:  NLM     Status:  MEDLINE    
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.
Roland Hany; Christine Böhlen; Thomas Geiger; Manfred Schmid; Manfred Zinn
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Biomacromolecules     Volume:  5     ISSN:  1525-7797     ISO Abbreviation:  Biomacromolecules     Publication Date:    2004 Jul-Aug
Date Detail:
Created Date:  2004-07-12     Completed Date:  2005-02-09     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  100892849     Medline TA:  Biomacromolecules     Country:  United States    
Other Details:
Languages:  eng     Pagination:  1452-6     Citation Subset:  IM    
Swiss Federal Laboratories for Materials Testing and Research (EMPA), CH-8600 Dübendorf, Switzerland.
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MeSH Terms
Acids / chemistry*
Biofilms / drug effects
Cinnamates / chemistry
Hydroxy Acids / chemistry
Molecular Structure
Polyesters / chemical synthesis*,  metabolism*,  toxicity
Pseudomonas putida / chemistry
Sulfates / chemistry
Toxicity Tests
Reg. No./Substance:
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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