A stereoselective synthesis of a C-glycosylated peptoid building block

被引：32

作者：

Dechantsreiter, MA ^{[1
]}

Burkhart, F ^{[1
]}

Kessler, H ^{[1
]}

机构：

[1] Tech Univ Munich, Inst Organ Chem & Biochem, D-85747 Garching, Germany

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 3-4期

关键词：

D O I：

10.1016/S0040-4039(97)10566-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A C-glycosylated peptoid analogue of the Ser-O-GlcNAc with a single carbon chain between the sugar residue and the peptoid was prepared by the coupling of a peptoid aldehyde with a glycosyl dianion of the glucosamine. (C) 1997 Elsevier Science Ltd. All rights reserved.

引用

页码：253 / 254

页数：2

共 11 条

[1] NEW METHOD FOR DEOXYGENATION OF SECONDARY ALCOHOLS [J].

BARTON, DHR ;

MCCOMBIE, SW .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (16) :1574-1585

[2] Stereoselective synthesis of a C-glycosidic analog of N-glucoasparagine [J].

Burkhart, F ;

Hoffmann, M ;

Kessler, H .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (11) :1191-1192

[3]

HART GW, 1989, ANNU REV BIOCHEM, V58, P841

[4] C-glycoside analogues of N-4-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-L-asparagine: Synthesis and conformational analysis of a cyclic C-glycopeptide [J].

Hoffmann, M ;

Burkhart, F ;

Hessler, G ;

Kessler, H .

HELVETICA CHIMICA ACTA, 1996, 79 (06) :1519-1532

[5] Competition of deprotonation and tin-lithium exchange in the generation of a glycosyl dianion [J].

Hoffmann, M ;

Kessler, H .

TETRAHEDRON LETTERS, 1997, 38 (11) :1903-1906

[6] PEPTOIDS - A NEW APPROACH TO THE DEVELOPMENT OF PHARMACEUTICALS [J].

KESSLER, H .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1993, 32 (04) :543-544

[7] Oligomeric glycopeptidomimetics bearing the cancer related T-N-antigen [J].

Kim, JM ;

Roy, R .

TETRAHEDRON LETTERS, 1997, 38 (20) :3487-3490

[8] PROTEOLYTIC STUDIES OF HOMOLOGOUS PEPTIDE AND N-SUBSTITUTED GLYCINE PEPTOID OLIGOMERS [J].

MILLER, SM ;

SIMON, RJ ;

NG, S ;

ZUCKERMANN, RN ;

KERR, JM ;

MOOS, WH .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1994, 4 (22) :2657-2662

[9] N-METHOXY-N-METHYLAMIDES AS EFFECTIVE ACYLATING AGENTS [J].

NAHM, S ;

WEINREB, SM .

TETRAHEDRON LETTERS, 1981, 22 (39) :3815-3818

[10] FIRST SYNTHESIS OF N-LINKED-GLYCOPEPTOID AS NEW GLYCOPEPTIDOMIMETICS [J].

SAHA, UK ;

ROY, R .

TETRAHEDRON LETTERS, 1995, 36 (21) :3635-3638

← 1 2 →