Synthesis of new peptidic glycoclusters derived from β-alanine

被引：15

作者：

Sato, K ^{[1
]}

Hada, N ^{[1
]}

Takeda, T ^{[1
]}

机构：

[1] Kyoritsu Coll Pharmaceut Sci, Minato Ku, Tokyo 1058512, Japan

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 52期

关键词：

glycocluster; beta-peptide; D-galactose; unit synthesis; carbohydrate-protein interaction;

D O I：

10.1016/j.tetlet.2003.10.073

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of an asymmetric glycocluster 1 has been achieved by coupling of a sugar unit with the beta-alanine polypeptide, the principal chain, and combining a carbohydrate chain with the side chain causing it to branch from the N terminal. The synthesis of this side chain multivalent ligands is based on the scaffolding of some omega-amino acid (glycine, beta-alanine, and GABA) derivatives. This method facilitated the synthesis of the cluster, of which the length of each unit differs. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：9331 / 9335

页数：5

共 14 条

[1] A convergent synthesis of a carbohydrate-containing dendrimer [J].

Ashton, PR ;

Boyd, SE ;

Brown, CL ;

Jayaraman, N ;

Stoddart, JF .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (07) :732-735

[2]

Fukuda M., 1994, MOL GLYCOBIOLOGY

[3] 2-NITROBENZENESULFONAMIDES AND 4-NITROBENZENESULFONAMIDES - EXCEPTIONALLY VERSATILE MEANS FOR PREPARATION OF SECONDARY-AMINES AND PROTECTION OF AMINES [J].

FUKUYAMA, T ;

JOW, CK ;

CHEUNG, M .

TETRAHEDRON LETTERS, 1995, 36 (36) :6373-6374

[4]

KHAN SH, 1996, MODERN METHODS CARBO, P378

[5] Assembly of dendritic glycoclusters from monomeric mannose building blocks [J].

Langer, P ;

Ince, SJ ;

Ley, SV .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (23) :3913-3915

[6] SELECTIN-CARBOHYDRATE INTERACTIONS AND THE INITIATION OF THE INFLAMMATORY RESPONSE [J].

LASKY, LA .

ANNUAL REVIEW OF BIOCHEMISTRY, 1995, 64 :113-139

[7] NEW SYNTHETIC CLUSTER LIGANDS FOR GALACTOSE/N-ACETYLGALACTOSAMINE-SPECIFIC LECTIN OF MAMMALIAN LIVER [J].

LEE, RT ;

LIN, P ;

LEE, YC .

BIOCHEMISTRY, 1984, 23 (18) :4255-4261

[8] CARBOHYDRATE-PROTEIN INTERACTIONS - BASIS OF GLYCOBIOLOGY [J].

LEE, YC ;

LEE, RT .

ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (08) :321-327

[9]

LEE YC, 1982, GLYCOCONJUGATES, V4, P57

[10] The syntheses of δ-NCS-butyl α-L-fucosides and fucobiosides and their clustering to triantennary glycomimetics [J].

Lindhorst, TK ;

Ludewig, M ;

Thiem, J .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 1998, 17 (07) :1131-1149

← 1 2 →