Asparagine surrogates for the assembly of N-linked glycopeptide mimetics by chemoselective ligation

被引：48

作者：

Peluso, S ^{[1
]}

Imperiali, B ^{[1
]}

机构：

[1] MIT, Dept Chem, Cambridge, MA 02139 USA

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 11期

基金：

美国国家卫生研究院;

关键词：

glycopeptide mimetic; solid-phase synthesis; chemoselective ligation;

D O I：

10.1016/S0040-4039(01)00104-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Alanine-beta -hydroxylamine (A betax) and alanine-beta -hydrazide (A betaz) have been developed as asparagine surrogates for the assembly of N-linked glycopeptide mimetics by chemoselective ligation. The utility of these residues is illustrated with the synthesis of the oligosaccharyl transferase substrate mimetics 1 and 2, and conjugation thereof with GlcNAc to obtain the N-glycopeptide mimetics 3 and 4. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：2085 / 2087

页数：3

共 5 条

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Shin, I
Park, S
Kim, KS
Cho, JW
Lim, D
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2002, 23 (01) : 15 - 16
[2] Synthesis of an N-linked glycopeptide from vitamin K-dependent protein S
Holm, B
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Kihlberg, J
TETRAHEDRON, 1998, 54 (39) : 11995 - 12006
[3] Solid-phase synthesis of unprotected N-glycopeptide building blocks for SPOT synthesis of N-linked glycopeptides
Jobron, L
Hummel, G
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2000, 39 (09) : 1621 - +
[4] Solid-phase synthesis of the CD52 glycopeptide carrying an N-linked core pentasaccharide structure
Guo, ZW
Nakahara, Y
Nakahara, Y
Ogawa, T
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (13-14): : 1464 - 1466
[5] A facile synthesis of the fucosylated N-linked glycan core and its application to solid-phase synthesis of CD52 glycopeptide
Shao, N
Guo, ZW
POLISH JOURNAL OF CHEMISTRY, 2005, 79 (02) : 297 - 307

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