Synthesis of Threefold Glycosylated Proteins using Click Chemistry and Genetically Encoded Unnatural Amino Acids

被引：49

作者：

Kaya, Emine ^{[1
]}

Gutsmiedl, Katrin ^{[1
]}

Vrabel, Milan ^{[1
]}

Mueller, Markus ^{[1
]}

Thumbs, Peter ^{[1
]}

Carell, Thomas ^{[1
]}

机构：

[1] Ludwig Maximilians Univ Munchen, Dept Chem & Biochem, Ctr Integrated Prot Sci CiPSM, D-81377 Munich, Germany

来源：

CHEMBIOCHEM | 2009年 / 10卷 / 18期

关键词：

amber suppression; amino acids; click chemistry; protein glycosylation; pyrrolysine; TRANSFER-RNA SYNTHETASE; SITE-SPECIFIC INCORPORATION; NATIVE CHEMICAL LIGATION; GLYCOPROTEIN-SYNTHESIS; RECOMBINANT PROTEINS; TERMINAL ALKYNES; SOLID-PHASE; PYRROLYSINE; CODE; AZIDES;

D O I：

10.1002/cbic.200900625

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Click to convert. Three encoded alkyne and alkene amino acids were incorporated into yellow fluorescent protein (YFP) and subsequently glycosylated by using the CuI catalyzed click reaction, as illustrated in the scheme. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

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收藏

页码：2858 / 2861

页数：4

相关论文

共 60 条

[1] SITE-SPECIFIC INCORPORATION OF NONNATURAL RESIDUES DURING INVITRO PROTEIN-BIOSYNTHESIS WITH SEMISYNTHETIC AMINOACYL-TRANSFER RNAS [J].

BAIN, JD ;

DIALA, ES ;

GLABE, CG ;

WACKER, DA ;

LYTTLE, MH ;

DIX, TA ;

CHAMBERLIN, AR .

BIOCHEMISTRY, 1991, 30 (22) :5411-5421

[2] Bioorthogonal click chemistry: Covalent labeling in living systems [J].

Baskin, Jeremy M. ;

Bertozzi, Carolyn R. .

QSAR & COMBINATORIAL SCIENCE, 2007, 26 (11-12) :1211-1219

[3] Combined Approaches to the Synthesis and Study of Glycoproteins [J].

Bernardes, Goncalo J. L. ;

Castagner, Bastien ;

Seeberger, Peter H. .

ACS CHEMICAL BIOLOGY, 2009, 4 (09) :703-713

[4] Tetrazine ligation: Fast bioconjugation based on inverse-electron-demand Diels-Alder reactivity [J].

Blackman, Melissa L. ;

Royzen, Maksim ;

Fox, Joseph M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (41) :13518-+

[5] Directed DNA metallization [J].

Burley, GA ;

Gierlich, J ;

Mofid, MR ;

Nir, H ;

Tal, S ;

Eichen, Y ;

Carell, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (05) :1398-1399

[6] A Facile System for Encoding Unnatural Amino Acids in Mammalian Cells [J].

Chen, Peng R. ;

Groff, Dan ;

Guo, Jiantao ;

Ou, Weijia ;

Cellitti, Susan ;

Geierstanger, Bernhard H. ;

Schultz, Peter G. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (22) :4052-4055

[7]

Chen PR., 2009, Angew. Chem, V121, P4112

[8] Glycan Engineering and Production of 'Humanized' Glycoprotein in Yeast Cells [J].

Chiba, Yasunori ;

Akeboshi, Hiromi .

BIOLOGICAL & PHARMACEUTICAL BULLETIN, 2009, 32 (05) :786-795

[9] Second-generation difluorinated cyclooctynes for copper-free click chemistry [J].

Codelli, Julian A. ;

Baskin, Jeremy M. ;

Agard, Nicholas J. ;

Berozzi, Carolyn R. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (34) :11486-11493

[10]

DANISHEFSKY SJ, 2005, GORD RES C NAT PROD

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