Stereoselective synthesis of β-linked TBDMS-protected chitobiose-asparagine:: a versatile building block for amyloidogenic glycopeptides

被引：17

作者：

Bosques, CJ ^{[1
]}

Tai, VWF ^{[1
]}

Imperiali, B ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 41期

基金：

美国国家卫生研究院;

关键词：

glycopeptide synthesis; amyloidogenic peptide; protein glycosylation;

D O I：

10.1016/S0040-4039(01)01524-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple and efficient synthesis of a Fmoc-L-Asn[beta -chitobiose(TBDMS)(5)]-OH with selectivity for the beta -linked carbohydrate is described. The Utility Of this building block is illustrated in the synthesis of a glycosylated amyloidogenic peptide representing the 175-195(+) fragment of the mouse prion protein (PrPGP). (C) 2001 Elsevier Science Ltd. All rights reserved.

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收藏

页码：7207 / 7210

页数：4

相关论文

共 14 条

[1] Recent advances in the synthesis of complex N-glycopeptides [J].

Arsequell, G ;

Valencia, G .

TETRAHEDRON-ASYMMETRY, 1999, 10 (16) :3045-3094

[2] Use of acid-labile protective groups for carbohydrate moieties in synthesis of glycopeptides related to type II collagen [J].

Broddefalk, J ;

Bergquist, KE ;

Kihlberg, J .

TETRAHEDRON, 1998, 54 (39) :12047-12070

[3] PROTECTED-MODE SYNTHESIS OF N-LINKED GLYCOPEPTIDES - SINGLE-STEP PREPARATION OF BUILDING-BLOCKS AS PERACETYL GLYCOSYLATED N-ALPHA-FMOC ASPARAGINE OPFP ESTERS [J].

CHRISTIANSENBRAMS, I ;

MELDAL, M ;

BOCK, K .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (13) :1461-1471

[4]

Danishefsky SJ, 2000, ANGEW CHEM INT EDIT, V39, P836, DOI 10.1002/(SICI)1521-3773(20000303)39:5<836::AID-ANIE836>3.0.CO

[5]

2-I

[6] NEW ALLYL GROUP ACCEPTORS FOR PALLADIUM-CATALYZED REMOVAL OF ALLYLIC PROTECTIONS AND TRANSACYLATION OF ALLYL CARBAMATES [J].

DESSOLIN, M ;

GUILLEREZ, MG ;

THIERIET, N ;

GUIBE, F ;

LOFFET, A .

TETRAHEDRON LETTERS, 1995, 36 (32) :5741-5744

[7] Synthesis of an N-linked glycopeptide from vitamin K-dependent protein S [J].

Holm, B ;

Linse, S ;

Kihlberg, J .

TETRAHEDRON, 1998, 54 (39) :11995-12006

[8]

Jobron L, 2000, ANGEW CHEM INT EDIT, V39, P1621, DOI 10.1002/(SICI)1521-3773(20000502)39:9<1621::AID-ANIE1621>3.0.CO

[9]

2-P

[10] A NEW SIMPLE SYNTHESIS OF AMINO SUGAR BETA-D-GLYCOSYLAMINES [J].

LIKHOSHERSTOV, LM ;

NOVIKOVA, OS ;

DEREVITSKAJA, VA ;

KOCHETKOV, NK .

CARBOHYDRATE RESEARCH, 1986, 146 (01) :C1-C5