Molecular design and biological potential of galacto-type trehalose as a nonnatural ligand of Shiga toxins

被引:33
作者
Dohi, H
Nishida, Y [1 ]
Furuta, Y
Uzawa, H
Yokoyama, S
Ito, S
Mori, H
Kobayashi, K
机构
[1] Nagoya Univ, Grad Sch Engn, Dept Mol Design & engn, Chikusa Ku, Nagoya, Aichi 4648603, Japan
[2] Natl Inst Adv Ind Sci & Technol, Tsukuba, Ibaraki 3058565, Japan
[3] Gifu Pharmaceut Univ, Dept Publ Hlth Pharm, Gifu 5028585, Japan
关键词
D O I
10.1021/ol017135+
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] alacto-type trehalose, a "C-4 epimer of trehalose", possesses a stereochemical structure around the alpha(1-1)-linkage analogous to that of the globoblosyl alpha(1-4)-linkage in Gb(2) and Gb(3) ceramides, which are known as the ligands of Shiga toxins produced by pathogenic E. coli. This paper presents evidence supporting the new idea of using a trehalosyl alpha(1-1)-linkage as a substitute for the galactobiosyl alpha(1-4)-linkage.
引用
收藏
页码:355 / 357
页数:3
相关论文
共 20 条
[1]   Influence of phospholipid chain length on verotoxin/globotriaosyl ceramide binding in model membranes: Comparison of a supported bilayer film and liposomes [J].
Arab, S ;
Lingwood, CA .
GLYCOCONJUGATE JOURNAL, 1996, 13 (02) :159-166
[2]   Synthesis of α- and β-carbon-linked serine analogues of the Pk trisaccharide [J].
Debenham, SD ;
Cossrow, J ;
Toone, EJ .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (25) :9153-9163
[3]   Synthesis of an artificial glycoconjugate polymer carrying Pk-antigenic trisaccharide and its potent neutralization activity against Shiga-like toxin [J].
Dohi, H ;
Nishida, Y ;
Mizuno, M ;
Shinkai, M ;
Kobayashi, T ;
Takeda, T ;
Uzawa, H ;
Kobayashi, K .
BIOORGANIC & MEDICINAL CHEMISTRY, 1999, 7 (09) :2053-2062
[4]  
Dohi H, 2001, SYNLETT, P1446
[5]   Rational design and synthesis of a 1,1-linked disaccharide that is 5 times as active as sialyl Lewis X in binding to E-selectin [J].
Hiruma, K ;
Kajimoto, T ;
WeitzSchmidt, G ;
Ollmann, I ;
Wong, CH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (39) :9265-9270
[6]  
KAWAGISHI H, 1994, J BIOL CHEM, V269, P1375
[7]   Shiga-like toxins are neutralized by tailored multivalent carbohydrate ligands [J].
Kitov, PI ;
Sadowska, JM ;
Mulvey, G ;
Armstrong, GD ;
Ling, H ;
Pannu, NS ;
Read, RJ ;
Bundle, DR .
NATURE, 2000, 403 (6770) :669-672
[8]   PURIFICATION AND CRYSTALLIZATION OF SHIGA TOXIN FROM SHIGELLA-DYSENTERIAE [J].
KOZLOV, YV ;
CHERNAIA, MM ;
FRASER, ME ;
JAMES, MNG .
JOURNAL OF MOLECULAR BIOLOGY, 1993, 232 (02) :704-706
[9]   CARBOHYDRATE-PROTEIN INTERACTIONS - BASIS OF GLYCOBIOLOGY [J].
LEE, YC ;
LEE, RT .
ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (08) :321-327
[10]  
LINDBERG AA, 1987, J BIOL CHEM, V262, P1779