title: Carbohydrate-appended curdlans as a new family of glycoclusters with binding properties both for a polynucleotide and lectins.
abstract: Beta-1,3-glucans having carbohydrate-appendages (alpha-D-mannoside, N-acetyl-beta-D-glucosaminide and beta-lactoside) at the C6-position of every repeating unit can be readily prepared from curdlan (a linear beta-1,3-glucan) through regioselective bromination/azidation to afford 6-azido-6-deoxycurdlan followed by chemo-selective Cu(i)-catalyzed [3 + 2]-cycloaddition with various carbohydrate modules having a terminal alkyne. The resultant carbohydrate-appended curdlans can interact with polycytosine to form stable macromolecular complexes consistent with two polysaccharide strands and one polycytosine strand. Furthermore, these macromolecular complexes show strong and specific affinity toward carbohydrate-binding proteins (lectins). Therefore, one can utilize these carbohydrate-appended curdlans as a new family of glycoclusters.
authors.affiliation: Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University, Motooka 744, Nishi-ku, Fukuoka 819-0395, Japan.
authors.forename: Teruaki
authors.initials: T
authors.lastname: Hasegawa
authors.forename: Munenori
authors.initials: M
authors.lastname: Numata
authors.forename: Shiro
authors.initials: S
authors.lastname: Okumura
authors.forename: Taro
authors.initials: T
authors.lastname: Kimura
authors.forename: Kazuo
authors.initials: K
authors.lastname: Sakurai
authors.forename: Seiji
authors.initials: S
authors.lastname: Shinkai
mesh_terms: D000480:Alkynes / Q000737:chemistry; D001386:Azides / Q000737:chemistry; D002384:Catalysis; D002942:Circular Dichroism; D003300:Copper / Q000737:chemistry; D003596:Cytosine / Q000737:chemistry; D006031:Glycosylation; D037102:Lectins / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011119:Polynucleotides / Q000737:chemistry*; D012997:Solvents; D020349:Surface Plasmon Resonance; D047071:beta-Glucans / Q000737:chemistry*
chemical_list: D000480:Alkynes; D001386:Azides; D037102:Lectins; D011119:Polynucleotides; D012997:Solvents; D047071:beta-Glucans; C038459:curdlan; D003300:Copper; D003596:Cytosine