Chemical synthesis of sulfated oligosaccharides with a β-D-Gal-(1→3)-[β-D-Gal-(1→4)-(α-L-Fuc(1→3)-β-D-GlcNAc-(1→6)]-α-D-GalNAc sequence

被引:22
作者
Xia, J [1 ]
Srikrishnan, T [1 ]
Alderfer, JL [1 ]
Jain, RK [1 ]
Piskorz, CF [1 ]
Matta, KL [1 ]
机构
[1] New York State Dept Hlth, Roswell Pk Canc Inst, Buffalo, NY 14263 USA
关键词
chemical synthesis; 2D DQF-COSY; 2D ROESY; sulfated oligosaccharides; crystallography;
D O I
10.1016/S0008-6215(00)00211-1
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The syntheses of two sulfated pentasaccharides: beta -D-Gal6SO(3)Na-(1 --> 3)-[beta -D-Gal-(1 --> 4)-alpha -L-Fuc-(1 --> 3)-beta -D-Glc-NAc-(1 --> 6)1-alpha -D-GalNAc --> OMe (1) and beta -D-Gal6SO(3)Na-(1 --> 3)-[beta -D-Gal-(1 --> 4)-alpha -L-Fuc-(1 --> 3)-beta -D-GlcNAc6SO(3)Na-(1 --> 6)]-alpha -D-GalNAc --> OMe (2) by using Lewis(X) trisaccharides 12 and 16 as glycosyl donors are described. Sulfated oligosaccharides 1-2 and intermediate compounds are fully characterized by 2D H-1-H-1 DQF-COSY and 2D ROESY experiments. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:561 / 577
页数:17
相关论文
共 27 条
[11]   Therapeutic inhibition of carbohydrate-protein interactions in vivo [J].
Lowe, JB ;
Ward, PA .
JOURNAL OF CLINICAL INVESTIGATION, 1997, 99 (05) :822-826
[12]   A convenient synthesis of peracetylated glycosyl halides using bismuth(III) halides as catalysts [J].
Montero, JL ;
Winum, JY ;
Leydet, A ;
Kamal, M ;
Pavia, AA ;
Roque, JP .
CARBOHYDRATE RESEARCH, 1997, 297 (02) :175-180
[13]   AN EFFICIENT METHOD FOR GLUCOSYLATION OF HYDROXY COMPOUNDS USING GLUCOPYRANOSYL FLUORIDE [J].
MUKAIYAMA, T ;
MURAI, Y ;
SHODA, S .
CHEMISTRY LETTERS, 1981, (03) :431-432
[14]  
Ogawa S, 1998, EUR J ORG CHEM, V1998, P1099, DOI 10.1002/(SICI)1099-0690(199806)1998:6<1099::AID-EJOC1099>3.0.CO
[15]  
2-R
[16]   SYNTHETIC STUDIES ON CELL-SURFACE GLYCANS .4. RECONSTRUCTION OF GLYCAN CHAINS OF GLYCOPROTEIN - BRANCHING MANNOPENTAOSIDE AND MANNOHEXAOSIDE [J].
OGAWA, T ;
SASAJIMA, K .
TETRAHEDRON, 1981, 37 (16) :2787-2792
[17]   Leukocyte adhesion - Two selectins converge on sulphate [J].
Rosen, SD ;
Bertozzi, CR .
CURRENT BIOLOGY, 1996, 6 (03) :261-&
[18]   Inhibition of L-selectin-mediated leukocyte rolling by synthetic glycoprotein mimics [J].
Sanders, WJ ;
Gordon, EJ ;
Dwir, O ;
Beck, PJ ;
Alon, R ;
Kiessling, LL .
JOURNAL OF BIOLOGICAL CHEMISTRY, 1999, 274 (09) :5271-5278
[19]   Fucosylation of disaccharide precursors of sialyl Lewis(X) inhibit selectin-mediated cell adhesion [J].
Sarkar, AK ;
Rostand, KS ;
Jain, RK ;
Matta, KL ;
Esko, JD .
JOURNAL OF BIOLOGICAL CHEMISTRY, 1997, 272 (41) :25608-25616
[20]   AN EFFICIENT APPROACH TO O-GLYCOSIDES THROUGH CUBR2 -BU4NBR MEDIATED ACTIVATION OF GLYCOSIDES [J].
SATO, S ;
MORI, M ;
ITO, Y ;
OGAWA, T .
CARBOHYDRATE RESEARCH, 1986, 155 :C6-C10