Visualizing metabolically labeled glycoconjugates of living cells by copper-free and fast huisgen cycloadditions

被引：739

作者：

Ning, Xinghai ^{[1
]}

Guo, Jun ^{[1
]}

Wolfert, Margreet A. ^{[1
]}

Boons, Geert-Jan ^{[1
]}

机构：

[1] Univ Georgia, Complex Carbohydrate Res Ctr, Athens, GA 30602 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 12期

关键词：

azides; carbohydrates; click chemistry; glycoconjugates;

D O I：

10.1002/anie.200705456

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Presented) CuI-free click: 4-Dibenzocyclooctynol reacts, in the absence of a CuI catalyst, exceptionally fast with azido-containing saccharides and amino acids to give stable triazoles. A biotin-modified derivative is ideally suited for visualizing and tracking glycoconjugates of living cells that are metabolically labeled with azido-containing monosaccharides (see image). © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：2253 / 2255

页数：3

共 31 条

[1] A comparative study of bioorthogonal reactions with azides [J].

Agard, Nicholas J. ;

Baskin, Jeremy M. ;

Prescher, Jennifer A. ;

Lo, Anderson ;

Bertozzi, Carolyn R. .

ACS CHEMICAL BIOLOGY, 2006, 1 (10) :644-648

[2] A strain-promoted [3+2] azide-alkyne cycloaddition for covalent modification of blomolecules in living systems [J].

Agard, NJ ;

Prescher, JA ;

Bertozzi, CR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (46) :15046-15047

[3] Copper-free click chemistry for dynamic in vivo imaging [J].

Baskin, Jeremy M. ;

Prescher, Jennifer A. ;

Laughlin, Scott T. ;

Agard, Nicholas J. ;

Chang, Pamela V. ;

Miller, Isaac A. ;

Lo, Anderson ;

Codelli, Julian A. ;

Bertozzi, Carolyn R. .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2007, 104 (43) :16793-16797

[4] An expanded eukaryotic genetic code [J].

Chin, JW ;

Cropp, TA ;

Anderson, JC ;

Mukherji, M ;

Zhang, ZW ;

Schultz, PG .

SCIENCE, 2003, 301 (5635) :964-967

[5] Recent applications of the CuI-catalysed Huisgen azide-alkyne 1,3-dipolar cycloaddition reaction in carbohydrate chemistry [J].

Dedola, Simone ;

Nepogodiev, Sergey A. ;

Field, Robert A. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (07) :1006-1017

[6] Click chemistry as a reliable method for the high-density postsynthetic functionalization of alkyne-modified DNA [J].

Gierlich, Johannes ;

Burley, Glenn A. ;

Gramlich, Philipp M. E. ;

Hammond, David M. ;

Carell, Thomas .

ORGANIC LETTERS, 2006, 8 (17) :3639-3642

[7] Tailored glycoproteomics and glycan site mapping using saccharide-selective bioorthogonal probes [J].

Hanson, Sarah R. ;

Hsu, Tsui-Ling ;

Weerapana, Eranthie ;

Kishikawa, Kuniyuki ;

Simon, Gabriel M. ;

Cravatt, Benjamin F. ;

Wong, Chi-Huey .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (23) :7266-+

[8] DIRECT SYNTHESIS OF DIBENZOCYCLOOCTADIENES VIA DOUBLE ORTHO FRIEDEL-CRAFTS ALKYLATION BY USE OF ALDEHYDE-TRIMETHYLSILYL IODIDE ADDUCTS [J].

JUNG, ME ;

MOSSMAN, AB ;

LYSTER, MA .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (19) :3698-3701

[9] TOTAL SYNTHESIS OF ISOPAVINE AND INTERMEDIATES FOR THE PREPARATION OF SUBSTITUTED AMITRIPTYLINE ANALOGS - FACILE ROUTES TO SUBSTITUTED DIBENZOCYCLOOCTATRIENES AND DIBENZOCYCLOHEPTATRIENES [J].

JUNG, ME ;

MILLER, SJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (08) :1984-1992

[10] A tagging-via-substrate technology for detection and proteomics of farnesylated proteins [J].

Kho, Y ;

Kim, SC ;

Jiang, C ;

Barma, D ;

Kwon, SW ;

Cheng, JK ;

Jaunbergs, J ;

Weinbaum, C ;

Tamanoi, F ;

Falck, J ;

Zhao, YM .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (34) :12479-12484

← 1 2 3 4 →