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Advanced functionalization of polyhydroxyalkanoate via the UV-initiated thiol-ene click reaction
| 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 link.springer.com |
| Type: | article (author version) |
| URI: | http://hdl.handle.net/2115/65179 |
| 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)
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Submitter: 田島 健次
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