PMID- 26743654
OWN - NLM
STAT- MEDLINE
DCOM- 20170309
LR  - 20170309
IS  - 1432-0614 (Electronic)
IS  - 0175-7598 (Linking)
VI  - 100
IP  - 10
DP  - 2016 May
TI  - Advanced functionalization of polyhydroxyalkanoate via the UV-initiated thiol-ene 
      click reaction.
PG  - 4375-83
LID - 10.1007/s00253-015-7252-3 [doi]
AB  - 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. (1)H 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-L-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.
FAU - Tajima, Kenji
AU  - Tajima K
AD  - Division of Applied Chemistry, Faculty of Engineering, Hokkaido University, 
      N13W8, Kita-ku, Sapporo, 060-8628, Japan. ktajima@eng.hokudai.ac.jp.
FAU - Iwamoto, Kosuke
AU  - Iwamoto K
AD  - Division of Applied Chemistry, Faculty of Engineering, Hokkaido University, 
      N13W8, Kita-ku, Sapporo, 060-8628, Japan.
FAU - Satoh, Yasuharu
AU  - Satoh Y
AD  - Division of Applied Chemistry, Faculty of Engineering, Hokkaido University, 
      N13W8, Kita-ku, Sapporo, 060-8628, Japan.
FAU - Sakai, Ryosuke
AU  - Sakai R
AD  - Division of Applied Chemistry, Faculty of Engineering, Hokkaido University, 
      N13W8, Kita-ku, Sapporo, 060-8628, Japan.
AD  - Department of Materials Chemistry, Asahikawa National College of Technology, 
      Asahikawa, 071-8142, Japan.
FAU - Satoh, Toshifumi
AU  - Satoh T
AD  - Division of Applied Chemistry, Faculty of Engineering, Hokkaido University, 
      N13W8, Kita-ku, Sapporo, 060-8628, Japan.
FAU - Dairi, Tohru
AU  - Dairi T
AD  - Division of Applied Chemistry, Faculty of Engineering, Hokkaido University, 
      N13W8, Kita-ku, Sapporo, 060-8628, Japan. dairi@eng.hokudai.ac.jp.
LA  - eng
PT  - Journal Article
DEP - 20160107
PL  - Germany
TA  - Appl Microbiol Biotechnol
JT  - Applied microbiology and biotechnology
JID - 8406612
RN  - 0 (Fibronectins)
RN  - 0 (Polyesters)
RN  - 0 (Polyhydroxyalkanoates)
RN  - 459TN2L5F5 (poly(lactide))
RN  - 5UX2SD1KE2 (Cysteamine)
RN  - B03TJ3QU9M (3-Mercaptopropionic Acid)
RN  - TPY09G7XIR (Fluorescein)
SB  - IM
MH  - 3-Mercaptopropionic Acid/chemistry
MH  - Click Chemistry/*methods
MH  - Cysteamine/chemistry
MH  - Fibronectins/chemistry
MH  - Fluorescein/chemistry
MH  - Human Umbilical Vein Endothelial Cells
MH  - Humans
MH  - Magnetic Resonance Spectroscopy
MH  - Molecular Weight
MH  - Polyesters/chemistry
MH  - Polyhydroxyalkanoates/*chemistry
MH  - *Ultraviolet Rays
OTO - NOTNLM
OT  - Click chemistry
OT  - Double bond
OT  - Ene-thiol click reaction
OT  - Medium-chain length
OT  - Polyhydroxyalkanoate
EDAT- 2016/01/09 06:00
MHDA- 2017/03/10 06:00
CRDT- 2016/01/09 06:00
PHST- 2015/10/31 00:00 [received]
PHST- 2015/12/14 00:00 [accepted]
PHST- 2015/12/12 00:00 [revised]
PHST- 2016/01/09 06:00 [entrez]
PHST- 2016/01/09 06:00 [pubmed]
PHST- 2017/03/10 06:00 [medline]
AID - 10.1007/s00253-015-7252-3 [pii]
AID - 10.1007/s00253-015-7252-3 [doi]
PST - ppublish
SO  - Appl Microbiol Biotechnol. 2016 May;100(10):4375-83. doi: 
      10.1007/s00253-015-7252-3. Epub 2016 Jan 7.