A broadly applicable method for the efficient synthesis of α-O-linked glycopeptides and clustered sialic acid residues

被引：110

作者：

Schwarz, JB

Kuduk, SD

Chen, XT

Sames, D

Glunz, PW

Danishefsky, SJ

机构：

[1] Sloan Kettering Inst Canc Res, Bioorgan Chem Lab, New York, NY 10021 USA

[2] Columbia Univ, Dept Chem, New York, NY 10027 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1999年 / 121卷 / 12期

关键词：

D O I：

10.1021/ja9833265

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The total syntheses of complex sialylated cell-surface antigens have been accomplished. The target systems include 2.3-STF, STn, 2,6-STF, and glycophorin antigens. In addition,an alpha-O-linked serine glycoside of an entire Lewis blood group (Y) antigen has been assembled.

引用

收藏

页码：2662 / 2673

页数：12

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共 50 条

[1] A NEW STRATEGY FOR SOLID-PHASE SYNTHESIS OF O-GLYCOPEPTIDES [J].

BIELFELDT, T ;

PETERS, S ;

MELDAL, M ;

BOCK, K ;

PAULSEN, H .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1992, 31 (07) :857-859

[2] Glycoconjugates facing the outside world [J].

Carlstedt, I ;

Davies, JR .

BIOCHEMICAL SOCIETY TRANSACTIONS, 1997, 25 (01) :214-219

[3] Exploration of modalities in building α-O-linked systems through glycal assembly:: A total synthesis of the mucin-related F1α antigen [J].

Chen, XT ;

Sames, D ;

Danishefsky, SJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (31) :7760-7769

[4] Glycals in organic synthesis: The evolution of comprehensive strategies for the assembly of oligosaccharides and glycoconjugates of biological consequence [J].

Danishefsky, SJ ;

Bilodeau, MT .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (13-14) :1380-1419

[5]

DENINNO MP, 1991, SYNTHESIS-STUTTGART, P583

[6] Preparation of Tn and sialyl Tn building blocks used in Fmoc solid-phase synthesis of glycopeptide fragments from HIV gp120 [J].

Elofsson, M ;

Salvador, LA ;

Kihlberg, J .

TETRAHEDRON, 1997, 53 (01) :369-390

[7] HIGHLY STEREOSELECTIVE ALPHA-SIALYLATION - SYNTHESIS OF GM(3)-SACCHARIDE AND A BIS-SIALIC ACID UNIT [J].

ERCEGOVIC, T ;

MAGNUSSON, G .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (11) :3378-3384

[8] MUC-1 EPITHELIAL TUMOR MUCIN-BASED IMMUNITY AND CANCER VACCINES [J].

FINN, OJ ;

JEROME, KR ;

HENDERSON, RA ;

PECHER, G ;

DOMENECH, N ;

MAGARIANBLANDER, J ;

BARRATTBOYES, SM .

IMMUNOLOGICAL REVIEWS, 1995, 145 :61-89

[9]

FUJED P, 1987, GLYCONCONJUGATE J, V4, P97

[10]

FUKUDA M, 1986, J BIOL CHEM, V261, P2796

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