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Advanced functionalization of polyhydroxyalkanoate via the UV-initiated thiol-ene click reaction

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Title: Advanced functionalization of polyhydroxyalkanoate via the UV-initiated thiol-ene click reaction
Authors: Tajima, Kenji Browse this author →KAKEN DB
Iwamoto, Kosuke Browse this author
Satoh, Yasuharu Browse this author →KAKEN DB
Sakai, Ryosuke Browse this author
Satoh, Toshifumi Browse this author →KAKEN DB
Dairi, Tohru Browse this author →KAKEN DB
Keywords: Polyhydroxyalkanoate
Medium-chain length
Click chemistry
Double bond
Ene-thiol click reaction
Issue Date: May-2016
Publisher: Springer
Journal Title: Applied microbiology and biotechnology
Volume: 100
Issue: 10
Start Page: 4375
End Page: 4383
Publisher DOI: 10.1007/s00253-015-7252-3
PMID: 26743654
Abstract: Polyhydroxyalkanoates (PHAs) incorporating vinyl-bearing 3-hydroxyalkanoates were prepared in 8.5-12.9 g L-1 yield. The molar ratios (0-16 mol%) of the vinyl-bearing 3-hydroxyalkanoate derivatives were controlled by the continuous feeding of undecylenate at various concentrations. Subsequently, the PHAs were functionalized by UV-initiated thiol-ene click reaction and chemical modification. H-1 NMR spectra suggested that 3-mercaptopropionic acid and 2-aminoethanethiol were successfully introduced into the vinyl-bearing PHA. Subsequently, chemical modification using fluorescein or a fibronectin active fragment (GRGDS) was attempted. The former yielded a PHA derivative capable of emitting fluorescence under UV irradiation, which was useful for determining the miscibility of PHA in a composite film comprising poly-EY-lactic acid (PLLA) and PHA. In the latter case, PHA bearing GRGDS peptides exhibited cell adhesiveness, suggesting that its biocompatibility was improved upon peptide introduction. Taken together, the UV-initiated thiol-ene click reaction was demonstrated to be useful in PHA modification.
Rights: The final publication is available at
Type: article (author version)
Appears in Collections:工学院・工学研究院 (Graduate School of Engineering / Faculty of Engineering) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 田島 健次

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