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

Tajima, Kenji; Iwamoto, Kosuke; Satoh, Yasuharu; Sakai, Ryosuke; Satoh, Toshifumi; Dairi, Tohru

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

Tajima, Kenji; Iwamoto, Kosuke; Satoh, Yasuharu et al.

Applied microbiology and biotechnology, 2016, 100(10), 4375-4383

Permalink : https://hdl.handle.net/2115/65179

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アクセス権	open access
URI	https://hdl.handle.net/2115/65179
タイトル	Advanced functionalization of polyhydroxyalkanoate via the UV-initiated thiol-ene click reaction
著者	Tajima, Kenji ; Iwamoto, Kosuke ; Satoh, Yasuharu ; Sakai, Ryosuke ; Satoh, Toshifumi ; Dairi, Tohru
e-Rad_Researcher 00271643 著者名 Tajima, Kenji
著者名 Iwamoto, Kosuke
e-Rad_Researcher 30360928 著者名 Satoh, Yasuharu
著者名 Sakai, Ryosuke
e-Rad_Researcher 80291235 著者名 Satoh, Toshifumi
e-Rad_Researcher 70264679 著者名 Dairi, Tohru
言語	英語
キーワード	Polyhydroxyalkanoate
	Medium-chain length
	Click chemistry
	Double bond
	Ene-thiol click reaction
発行日	2016-05
出版者	Springer
収録物名	Applied microbiology and biotechnology
巻(号)	100(10)
ページ	4375-4383
抄録	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.
資源タイプ	学術雑誌論文
出版タイプ	Accepted Manuscript
権利情報	The final publication is available at link.springer.com
PISSN	0175-7598
関連情報	PMID 26743654
関連情報 (isVersionOf)	出版社版DOI https://doi.org/10.1007/s00253-015-7252-3