Synthesis of n-octyl 2,6-dideoxy-α-L-lyxo-hexopyranosyl-(1→2)-3-amino-3-deoxy-β-D-galactopyranoside, an analog of the H-disaccharide antigen

被引：5

作者：

Bai, Yu

Lin, Shuang-Jun

Qi, Guizhong

Palcic, Monica M.

Lowary, Todd L. ^{[1
]}

机构：

[1] Univ Alberta, Dept Chem, Gunning Lemieux Chem Ctr, Edmonton, AB T6G 2G2, Canada

[2] Univ Alberta, Alberta Ingenu Ctr Carbohydrate Sci, Gunning Lemieux Chem Ctr, Edmonton, AB T6G 2G2, Canada

[3] Carlsberg Lab, DK-2500 Copenhagen, Denmark

来源：

CARBOHYDRATE RESEARCH | 2006年 / 341卷 / 10期

基金：

加拿大自然科学与工程研究理事会;

关键词：

H-disaccharide antigen; blood group; synthesis; inhibitor; molecular recognition;

D O I：

10.1016/j.carres.2006.03.018

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 synthesis of an analog of the H-disaccharide antigen (2), in which the galactopyranosyl moiety bears an amino group at C-3 and the fucopyranosyl residue is deoxygenated at C-2, is reported. The key reaction in the preparation of 2 was the glycosylation of an appropriately protected n-octyl 3-azido-3-deoxy-galactopyranoside derivative with a 2,6-dideoxy thioglycoside promoted by 1-(phenylsulfinyl)piperidine and triflic anhydride. Disaccharide 2 is of interest in studies directed towards understanding the molecular basis of substrate recognition by the blood group A and B glycosyltransferases. (c) 2006 Elsevier Ltd. All rights reserved.

引用

收藏

页码：1702 / 1707

页数：6

相关论文

共 20 条

[1] Immunological aspects of blood transfusions [J].

Brand, A .

TRANSPLANT IMMUNOLOGY, 2002, 10 (2-3) :183-190

[2] SELECTIVE REMOVAL OF O-ACETYL GROUPS IN THE PRESENCE OF O-BENZOYL GROUPS BY ACID-CATALYZED METHANOLYSIS [J].

BYRAMOVA, NE ;

OVCHINNIKOV, MV ;

BACKINOWSKY, LV ;

KOCHETKOV, NK .

CARBOHYDRATE RESEARCH, 1983, 124 (01) :C8-C11

[3] 1-Benzenesulfinyl piperidine/trifluoromethanesulfonic anhydride: A potent combination of shelf-stable reagents for the low-temperature conversion of thioglycosides to glycosyl triflates and for the formation of diverse glycosidic linkages [J].

Crich, D ;

Smith, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (37) :9015-9020

[4] IODONIUM PROMOTED REACTIONS OF DISARMED THIOGLYCOSIDES [J].

KONRADSSON, P ;

UDODONG, UE ;

FRASERREID, B .

TETRAHEDRON LETTERS, 1990, 31 (30) :4313-4316

[5] Intracellular inhibition of blood group A glycosyltransferase [J].

Laferté, S ;

Chan, NWC ;

Sujino, K ;

Lowary, TL ;

Palcic, MM .

EUROPEAN JOURNAL OF BIOCHEMISTRY, 2000, 267 (15) :4840-4849

[6] THE EFFECT OF SUBSTITUTING KEY HYDROXYL-GROUPS BY AMINO-GROUPS ON THE BINDING OF THE LEWIS-B TETRASACCHARIDE BY A LECTIN AND A MONOCLONAL-ANTIBODY [J].

LEMIEUX, RU ;

SZWEDA, R ;

PASZKIEWICZHNATIW, E ;

SPOHR, U .

CARBOHYDRATE RESEARCH, 1990, 205 :C12-C17

[7] Differential recognition of the type I and IIH antigen acceptors by the human ABO(H) blood group A and B glycosyltransferases [J].

Letts, JA ;

Rose, NL ;

Fang, YR ;

Barry, CH ;

Borisova, SN ;

Seto, NOL ;

Palcic, MM ;

Evans, SV .

JOURNAL OF BIOLOGICAL CHEMISTRY, 2006, 281 (06) :3625-3632

[8] RECOGNITION OF SYNTHETIC O-METHYL, EPIMERIC, AND AMINO ANALOGS OF THE ACCEPTOR ALPHA-L-FUCP-(1-]2)-BETA-D-GALP-OR BY THE BLOOD-GROUP-A AND BLOOD-GROUP-B GENE-SPECIFIED GLYCOSYLTRANSFERASES [J].

LOWARY, TL ;

HINDSGAUL, O .

CARBOHYDRATE RESEARCH, 1994, 251 :33-67

[9] A single point mutation reverses the donor specificity of human blood group B-synthesizing galactosyltransferase [J].

Marcus, SL ;

Polakowski, R ;

Seto, NOL ;

Leinala, E ;

Borisova, S ;

Blancher, A ;

Roubinet, F ;

Evans, SV ;

Palcic, MM .

JOURNAL OF BIOLOGICAL CHEMISTRY, 2003, 278 (14) :12403-12405

[10] Unravelling the biochemical basis of blood group ABO and Lewis antigenic specificity [J].

Morgan, WTJ ;

Watkins, WM .

GLYCOCONJUGATE JOURNAL, 2000, 17 (7-9) :501-530