Polysialosides scaffolded on p-tert-butylcalix[4]arene

被引：70

作者：

Meunier, SJ ^{[1
]}

Roy, R ^{[1
]}

机构：

[1] UNIV OTTAWA,DEPT CHEM,OTTAWA,ON K1N 6N5,CANADA

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 31期

基金：

加拿大自然科学与工程研究理事会;

关键词：

D O I：

10.1016/0040-4039(96)01167-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

p-Tert-butylcalix[4]arene (1) was transformed into known tetraethyl ester 2 to provide cone-shaped calix[4]arene used for the scaffolding of tetravalent alpha-sialoside. Ester 2 was transformed into acid chloride 4 which after treatment with mono-Boc-1,4-butanediamine, trifluoroacetolysis and N-chloroacetylation afforded tetraamine 7, Conjugation of alpha-thiosialoside 9 by nucleophilic substitution and deprotection furnished water-soluble tetravalent alpha-thiosialoside 12 which bound strongly to the plant lectin wheat germ agglutinin. Copyright (C) 1996 Elsevier Science Ltd

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页码：5469 / 5472

页数：4

相关论文

共 20 条

[1] FORMATION OF SOLVENT-SEPARATED ION-PAIRS IN CALIXARENE ESTER-ALKALI PICRATE COMPLEXES [J].

ARIMURA, T ;

KUBOTA, M ;

MATSUDA, T ;

MANABE, O ;

SHINKAI, S .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1989, 62 (05) :1674-1676

[2] SELECTIVE ALKALI-METAL CATION COMPLEXATION BY CHEMICALLY MODIFIED CALIXARENES .4. EFFECT OF SUBSTITUENT VARIATION ON THE NA+/K+ SELECTIVITY IN THE ESTER SERIES AND X-RAY CRYSTAL-STRUCTURE OF THE TRIFLUOROETHYL ESTER [J].

ARNAUDNEU, F ;

BARRETT, G ;

CREMIN, S ;

DEASY, M ;

FERGUSON, G ;

HARRIS, SJ ;

LOUGH, AJ ;

GUERRA, L ;

MCKERVEY, MA ;

SCHWINGWEILL, MJ ;

SCHWINTE, P .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1992, (07) :1119-1125

[3] SYNTHESIS OF SIALIC-ACID PSEUDOPOLYSACCHARIDES BY COUPLING OF SPACER-CONNECTED NEU5AC WITH ACTIVATED POLYMER [J].

BYRAMOVA, NE ;

MOCHALOVA, LV ;

BELYANCHIKOV, IM ;

MATROSOVICH, MN ;

BOVIN, NV .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 1991, 10 (04) :691-700

[4] INHIBITION OF INFLUENZA-A VIRUS HEMAGGLUTININ AND INDUCTION OF INTERFERON BY SYNTHETIC SIALYLATED GLYCOCONJUGATES [J].

GAMIAN, A ;

CHOMIK, M ;

LAFERRIERE, CA ;

ROY, R .

CANADIAN JOURNAL OF MICROBIOLOGY, 1991, 37 (03) :233-237

[5] MOLECULAR RECOGNITION OF BIVALENT SIALOSIDES BY INFLUENZA-VIRUS [J].

GLICK, GD ;

KNOWLES, JR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (12) :4701-4703

[6] SYNTHESES AND ION SELECTIVITY OF ALL CONFORMATIONAL ISOMERS OF TETRAKIS((ETHOXYCARBONYL)METHOXY)CALIX[4]ARENE [J].

IWAMOTO, K ;

SHINKAI, S .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (26) :7066-7073

[7] MICROBIAL RECOGNITION OF TARGET-CELL GLYCOCONJUGATES [J].

KARLSSON, KA .

CURRENT OPINION IN STRUCTURAL BIOLOGY, 1995, 5 (05) :622-635

[8]

MARRA A, 1994, ANGEW CHEM INT EDIT, V33, P2479

[9] SELECTION OF INFLUENZA-VIRUS VARIANTS BASED ON SIALYLOLIGOSACCHARIDE RECEPTOR SPECIFICITY [J].

PAULSON, JC ;

ROGERS, GN ;

CARROLL, SM ;

HIGA, HH ;

PRITCHETT, T ;

MILKS, G ;

SABESAN, S .

PURE AND APPLIED CHEMISTRY, 1984, 56 (07) :797-805

[10]

ROY R, 1994, METHOD ENZYMOL, V247, P351