Effect of (1-->3)- and (1-->4)-linkages of fully sulfated polysaccharides on their anticoagulant activity.
Chemically fully sulfated polysaccharides including xylan (-->4Xylbeta-(1-->4)Xylbeta1-->), amylose (-->4Glcalpha-(1-->4)Glcalpha1-->), cellulose (-->4Glcbeta-(1-->4)Glcbeta1-->), curdlan (-->3Glcbeta-(1-->3)Glcbeta1-->) and galactan (-->3Galbeta-(1-->3)Galbeta1-->), which have been isolated from Korean clam, were prepared, and their anticoagulant activity was investigated. The results strongly suggest that the activity might not be depending on anomeric configuration (alpha or beta) or monosaccharide species but on the glycosidic linkage, either (1-->3) or (1-->4). 1H NMR studies of these modified polysaccharides show that the neighboring sulfate groups at the C-2 and C-3 positions might have caused the conformational changes of each monosaccharide from 4C(1) to 1C(4). Furthermore, the effect of 6-sulfate residues on the anticoagulant activity was investigated using a specific desulfated reaction for the chemically fully sulfated polysaccharides. The 6-sulfate group is very important in determining anticoagulant activity of (1-->3)-linked polysaccharides, whereas the activity is not affected by presence or absence of the 6-sulfate group in (1-->4)-linked polysaccharides.
Chaidedgumjorn
Amornrut
A
Graduate School of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba-shi, Chiba 263-8522, Japan.
Toyoda
Hidenao
H
Woo
Eun Rhan
ER
Lee
Kyung Bok
KB
Kim
Yeong Shik
YS
Toida
Toshihiko
T
Imanari
Toshio
T
D000421:Alcaligenes / Q000737:chemistry; D000688:Amylose / Q000737:chemistry; D000925:Anticoagulants / Q000737:chemistry*; D029662:Betula / Q000737:chemistry; D002236:Carbohydrate Conformation; D002482:Cellulose / Q000737:chemistry; D005936:Glucans / Q000737:chemistry; D015394:Molecular Structure; D008970:Molecular Weight; D019906:Nuclear Magnetic Resonance, Biomolecular; D011134:Polysaccharides / Q000737:chemistry*; D011198:Solanum tuberosum / Q000737:chemistry; D013055:Spectrophotometry, Infrared; D013431:Sulfates / Q000737:chemistry*; D047071:beta-Glucans
D000925:Anticoagulants; D005936:Glucans; D011134:Polysaccharides; D013431:Sulfates; D047071:beta-Glucans; C038459:curdlan; D002482:Cellulose; D000688:Amylose