TY - JOUR
T1 - 'Click chemistry' on polysaccharides
T2 - A convenient, general, and monitorable approach to develop (1→3)-β-d-glucans with various functional appendages
AU - Hasegawa, Teruaki
AU - Umeda, Mariko
AU - Numata, Munenori
AU - Li, Chun
AU - Bae, Ah Hyun
AU - Fujisawa, Tomohisa
AU - Haraguchi, Shuichi
AU - Sakurai, Kazuo
AU - Shinkai, Seiji
N1 - Funding Information:
This work was supported by the Japan Science and Technology Agency, SORST Program. We also thank Mitsui Sugar Co. (Japan) for providing native SPG.
PY - 2006/1/16
Y1 - 2006/1/16
N2 - (1→3)-β-d-Glucans having various functional appendages (lactoside, ferrocene, pyrene, and porphyrin) can be prepared in an convenient, quantitative, and regioselective manner through regioselective bromination-azidation of curdlan to afford 6-azido-6-deoxycurdlan followed by chemoselective [3+2]-cycloadditions with various functional modules bearing a terminal alkyne group. The ability to monitor reaction conversions is an additional advantage of this synthetic approach over the conventional direct modifications on polysaccharides; the reaction can be readily monitored based on the intensity of azido peaks in the in situ attenuated total reflection infrared spectra.
AB - (1→3)-β-d-Glucans having various functional appendages (lactoside, ferrocene, pyrene, and porphyrin) can be prepared in an convenient, quantitative, and regioselective manner through regioselective bromination-azidation of curdlan to afford 6-azido-6-deoxycurdlan followed by chemoselective [3+2]-cycloadditions with various functional modules bearing a terminal alkyne group. The ability to monitor reaction conversions is an additional advantage of this synthetic approach over the conventional direct modifications on polysaccharides; the reaction can be readily monitored based on the intensity of azido peaks in the in situ attenuated total reflection infrared spectra.
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U2 - 10.1016/j.carres.2005.10.009
DO - 10.1016/j.carres.2005.10.009
M3 - Article
C2 - 16289495
AN - SCOPUS:29144474573
SN - 0008-6215
VL - 341
SP - 35
EP - 40
JO - Carbohydrate Research
JF - Carbohydrate Research
IS - 1
ER -