Glyco-SeS: Selenenylsulfide-mediated protein glycoconjugation - A new strategy in post-translational modification

被引：146

作者：

Gamblin, DP ^{[1
]}

Garnier, P ^{[1
]}

van Kasteren, S ^{[1
]}

Oldham, NJ ^{[1
]}

Fairbanks, AJ ^{[1
]}

Davis, BG ^{[1
]}

机构：

[1] Univ Oxford, Dyson Perrins Lab, Oxford OX1 3QY, England

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2004年 / 43卷 / 07期

基金：

英国生物技术与生命科学研究理事会;

关键词：

carbohydrates; glycoproteins; glycosylation; protein modifications; selenium;

D O I：

10.1002/anie.200352975

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Site-selective glycosylation by Se-S-mediated ligation has led to the efficient formation of a wide variety of conjugates 1 without the need for a large excess of the carbohydrate reagent. By this convergent method it was possible to introduce a heptasaccharide glycan selectively, and to perform a multiple site-selective chemical glycosylation of protein. A chemically Cysglycosylated glycoprotein was elaborated enzymatically.

引用

页码：828 / 833

页数：6

共 41 条

[1] Rapid induction of cell death by selenium-compromised thioredoxin reductase 1 but not by the fully active enzyme containing selenocysteine [J].

Anestål, K ;

Arnér, ESJ .

JOURNAL OF BIOLOGICAL CHEMISTRY, 2003, 278 (18) :15966-15972

[2]

Ashburner M, 2001, GENOME RES, V11, P1425

[3]

BEHAGHEL O, 1932, LIEBIGS ANN CHEM, V65, P812

[4]

BERGSON G, 1961, ARK KEMI, V17, P569

[5]

BONNER WA, 1951, J AM CHEM SOC, V73

[6] Glycomethanethiosulfonates: powerful reagents for protein glycosylation [J].

Davis, BG ;

Maughan, MAT ;

Green, MP ;

Ullman, A ;

Jones, JB .

TETRAHEDRON-ASYMMETRY, 2000, 11 (01) :245-262

[7] Chemical modification of biocatalysts [J].

Davis, BG .

CURRENT OPINION IN BIOTECHNOLOGY, 2003, 14 (04) :379-386

[8] Controlled site-selective glycosylation of proteins by a combined site-directed mutagenesis and chemical modification approach [J].

Davis, BG ;

Lloyd, RC ;

Jones, JB .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (26) :9614-9615

[9] Synthesis of glycoproteins [J].

Davis, BG .

CHEMICAL REVIEWS, 2002, 102 (02) :579-601

[10] Controlled site-selective protein glycosylation for precise glycan structure-catalytic activity relationships [J].

Davis, BG ;

Lloyd, RC ;

Jones, JB .

BIOORGANIC & MEDICINAL CHEMISTRY, 2000, 8 (07) :1527-1535

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