'Click chemistry' on polysaccharides: a convenient, general, and monitorable approach to develop (1-->3)-beta-D-glucans with various functional appendages.
(1-->3)-beta-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.
Hasegawa
Teruaki
T
Department of Chemistry and Biotechnology, Graduate School of Engineering, Kyushu University, Hakozaki, 6-10-1, Higashi-ku, Fukuoka 812-8581, Japan.
Umeda
Mariko
M
Numata
Munenori
M
Li
Chun
C
Bae
Ah-Hyun
AH
Fujisawa
Tomohisa
T
Haraguchi
Shuichi
S
Sakurai
Kazuo
K
Shinkai
Seiji
S
D000480:Alkynes / Q000737:chemistry; D001386:Azides / Q000737:chemistry; D019906:Nuclear Magnetic Resonance, Biomolecular; D011509:Proteoglycans; D017550:Spectroscopy, Fourier Transform Infrared; D047071:beta-Glucans / Q000138:chemical synthesis* / Q000737:chemistry
D000480:Alkynes; D001386:Azides; D011509:Proteoglycans; D047071:beta-Glucans; C010770:polysaccharide-K; C038459:curdlan