A HIGHLY CONVERGENT SYNTHESIS OF THE LEWIS(Y) BLOOD-GROUP DETERMINANT IN CONJUGATABLE FORM

被引:22
作者
BEHAR, V [1 ]
DANISHEFSKY, SJ [1 ]
机构
[1] MEM SLOAN KETTERING CANC CTR, NEW YORK, NY 10021 USA
关键词
D O I
10.1002/anie.199414681
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The versatility of glycals both as glycosyl donors and as glycosyl acceptors is used in the synthesis of the Lewisy determinant. This and the oligosaccharide described in the following communication consist of a determinant, a carbohydrate spacer, and a group suitable for the conjugation to a carrier protein. The spacer present in these new glycoproteins minimizes the likelihood that the protein carrier will distort the recognition property of the determinant. Copyright © 1994 by VCH Verlagsgesellschaft mbH, Germany
引用
收藏
页码:1468 / 1470
页数:3
相关论文
共 43 条
[1]   GENERAL-SYNTHESIS OF MODEL GLYCOPROTEINS - COUPLING OF ALKENYL GLYCOSIDES TO PROTEINS, USING REDUCTIVE OZONOLYSIS FOLLOWED BY REDUCTIVE AMINATION WITH SODIUM CYANOBOROHYDRIDE [J].
BERNSTEIN, MA ;
HALL, LD .
CARBOHYDRATE RESEARCH, 1980, 78 (01) :C1-C3
[2]   REMARKABLE REGIOSELECTIVITY IN THE CHEMICAL GLYCOSYLATION OF GLYCAL ACCEPTORS - A CONCISE SOLUTION TO THE SYNTHESIS OF SIALYL-LEWIS-X GLYCAL [J].
DANISHEFSKY, SJ ;
GERVAY, J ;
PETERSON, JM ;
MCDONALD, FE ;
KOSEKI, K ;
ORIYAMA, T ;
GRIFFITH, DA ;
WONG, CH ;
DUMAS, DP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (21) :8329-8331
[3]   AZAGLYCOSYLATION OF COMPLEX STANNYL ALKOXIDES WITH GLYCAL-DERIVED IODO SULFONAMIDES - A STRAIGHTFORWARD SYNTHESIS OF SIALYL-LEWIS-X ANTIGEN AND OTHER OLIGOSACCHARIDE DOMAINS [J].
DANISHEFSKY, SJ ;
KOSEKI, K ;
GRIFFITH, DA ;
GERVAY, J ;
PETERSON, JM ;
MCDONALD, FE ;
ORIYAMA, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (21) :8331-8333
[4]   VACCINATION WITH IRRADIATED TUMOR-CELLS ENGINEERED TO SECRETE MURINE GRANULOCYTE-MACROPHAGE COLONY-STIMULATING FACTOR STIMULATES POTENT, SPECIFIC, AND LONG-LASTING ANTITUMOR IMMUNITY [J].
DRANOFF, G ;
JAFFEE, E ;
LAZENBY, A ;
GOLUMBEK, P ;
LEVITSKY, H ;
BROSE, K ;
JACKSON, V ;
HAMADA, H ;
PARDOLL, D ;
MULLIGAN, RC .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1993, 90 (08) :3539-3543
[5]  
FUKUSHI Y, 1984, J BIOL CHEM, V259, P511
[6]  
FUKUSHI Y, 1984, J BIOL CHEM, V259, P4681
[7]   SULFONAMIDOGLYCOSYLATION OF GLYCALS - A ROUTE TO OLIGOSACCHARIDES WITH 2-AMINOHEXOSE SUBUNITS [J].
GRIFFITH, DA ;
DANISHEFSKY, SJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (15) :5811-5819
[8]  
HAKOMORI S, 1984, J BIOL CHEM, V259, P4672
[9]   ON THE DIRECT EPOXIDATION OF GLYCALS - APPLICATION OF A REITERATIVE STRATEGY FOR THE SYNTHESIS OF BETA-LINKED OLIGOSACCHARIDES [J].
HALCOMB, RL ;
DANISHEFSKY, SJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (17) :6661-6666
[10]   The structure of carbohydrates and their optical rotatory power Part III 4-galactosido-alpha-mannose and its derivatives [J].
Haworth, WN ;
Hirst, EL ;
Plant, MMT ;
Reynolds, RJW .
JOURNAL OF THE CHEMICAL SOCIETY, 1930, :2644-2653