Combinatorial synthesis of amino acid- and peptide-carbohydrate conjugates on solid phase

被引：20

作者：

Opatz, T ^{[1
]}

Kallus, C ^{[1
]}

Wunberg, T ^{[1
]}

Kunz, H ^{[1
]}

机构：

[1] Johannes Gutenberg Univ Mainz, Inst Organ Chem, D-55128 Mainz, Germany

来源：

TETRAHEDRON | 2004年 / 60卷 / 39期

关键词：

combinatorial chemistry; solid-phase synthesis; carbohydrates; peptidomimetics; scaffolds;

D O I：

10.1016/j.tet.2004.05.101

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Carbohydrates are useful polyfunctional scaffold molecules which allow the selective attachment of a number of different side chains. The combinatorial solid phase synthesis of diverse amino acid or peptide conjugates of a polyfunctional glucose scaffold based on a set of selectively removable and orthogonally stable protecting groups is described. The resulting carbohydrate-peptide hybrids constitute potential turn mimetics. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：8613 / 8626

页数：14

共 38 条

[11] A NEW METHOD FOR SYNTHESIS OF PEPTIDES - ACTIVATION OF CARBOXYL GROUP WITH DICYCLOHEXYLCARBODIIMIDE USING 1-HYDROXYBENZOTRIAZOLES AS ADDITIVES [J].

KONIG, W ;

GEIGER, R .

CHEMISCHE BERICHTE-RECUEIL, 1970, 103 (03) :788-&

[12] SYNTHESES OF ISOMALTOSE, ISOMALTOTETRAOSE, AND ISOMALTOOCTAOSE [J].

KOTO, S ;

UCHIDA, T ;

ZEN, S .

CHEMISTRY LETTERS, 1972, (11) :1049-1052

[13] HALIDE ION CATALYZED GLYCOSIDATION REACTIONS SYNTHESES OF ALPHA-LINKED DISACCHARIDES [J].

LEMIEUX, RU ;

HENDRIKS, KB ;

STICK, RV ;

JAMES, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (14) :4056-4062

[14] CHAIN REVERSALS IN PROTEINS [J].

LEWIS, PN ;

MOMANY, FA ;

SCHERAGA, HA .

BIOCHIMICA ET BIOPHYSICA ACTA, 1973, 303 (02) :211-229

[15] Novel tetrahydropyran-based peptidomimetics from a bioisosteric transformation of a tripeptide. Evidence of their activity at melanocortin receptors [J].

Mazur, AW ;

Kulesza, A ;

Mishra, RK ;

Cross-Doersen, D ;

Russell, AF ;

Ebetino, FH .

BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (14) :3053-3063

[16] Design, synthesis and preliminary biological evaluation of a focused combinatorial library of stereodiverse carbohydrate-scaffold-based peptidomimetics [J].

Moitessier, N ;

Dufour, S ;

Chrétien, F ;

Thiery, JP ;

Maigret, B ;

Chapleur, Y .

BIOORGANIC & MEDICINAL CHEMISTRY, 2001, 9 (02) :511-523

[17] 4-DIALKYLAMINOPYRIDINES AS ACYLATION CATALYSTS .5. SIMPLE METHOD FOR ESTERIFICATION OF CARBOXYLIC-ACIDS [J].

NEISES, B ;

STEGLICH, W .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1978, 17 (07) :522-524

[18]

Neises B., 1978, ANGEW CHEM, V90, P556, DOI [DOI 10.1002/ANGE.19780900718, 10.1002/ange.19780900718]

[19] Design, synthesis and biological evaluation of carbohydrate-based mimetics of cRGDFV [J].

Nicolaou, KC ;

Trujillo, JI ;

Chibale, K .

TETRAHEDRON, 1997, 53 (26) :8751-8778

[20] A MILD AND GENERAL-METHOD FOR THE SYNTHESIS OF O-GLYCOSIDES [J].

NICOLAOU, KC ;

SEITZ, SP ;

PAPAHATJIS, DP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (08) :2430-2434

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