N-Propargyloxycarbamate monosaccharides as metabolic chemical reporters of carbohydrate salvage pathways and protein glycosylation

被引：32

作者：

Bateman, Leslie A.

Zaro, Balyn W.

Chuh, Kelly N.

Pratt, Matthew R. ^{[1
]}

机构：

[1] Univ So Calif, Dept Chem, Los Angeles, CA 90089 USA

来源：

CHEMICAL COMMUNICATIONS | 2013年 / 49卷 / 39期

基金：

美国国家科学基金会;

关键词：

GLCNAC-MODIFIED PROTEINS; ACETYLGLUCOSAMINE;

D O I：

10.1039/c2cc37963e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Metabolic chemical reporters of glycosylation allow for the visualization and identification of a variety of glycoconjugates by taking advantage of the promiscuity of carbohydrate metabolism. Here we describe the synthesis and characterization of metabolic chemical reporters bearing an N-propargyloxycarbamate (Poc) group that creates discrimination between glycosylation pathways.

引用

收藏

页码：4328 / 4330

页数：3

相关论文

共 21 条

[1] Chemoselective Attachment of Small Molecule Effector Functionality to Human Adenoviruses Facilitates Gene Delivery to Cancer Cells [J].

Banerjee, Partha Sarathi ;

Ostapchuk, Philomena ;

Hearing, Patrick ;

Carrico, Isaac .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (39) :13615-13617

[2] GUEST EDITORIAL A Decade of Bioorthogonal Chemistry [J].

Bertozzi, Carolyn R. .

ACCOUNTS OF CHEMICAL RESEARCH, 2011, 44 (09) :651-653

[3] Metabolic cross-talk allows labeling of O-linked β-N-acetylglucosamine-modified proteins via the N-acetylgalactosamine salvage pathway [J].

Boyce, Michael ;

Carrico, Isaac S. ;

Ganguli, Anjali S. ;

Yu, Seok-Ho ;

Hangauer, Matthew J. ;

Hubbard, Sarah C. ;

Kohler, Jennifer J. ;

Bertozzi, Carolyn R. .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2011, 108 (08) :3141-3146

[4] Metabolic Labeling of Sialic Acids in Living Animals with Alkynyl Sugars [J].

Chang, Pamela V. ;

Chen, Xing ;

Smyrniotis, Chris ;

Xenakis, Alexander ;

Hu, Tianshun ;

Bertozzi, Carolyn R. ;

Wu, Peng .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (22) :4030-4033

[5] A metabolic labeling approach toward proteomic analysis of mucin-type O-linked glycosylation [J].

Hang, HC ;

Yu, C ;

Kato, DL ;

Bertozzi, CR .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2003, 100 (25) :14846-14851

[6] A bifunctional enzyme catalyzes the first two steps in N-acetylneuraminic acid biosynthesis of rat liver - Purification and characterization of UDP-N-acetylglucosamine 2-epimerase/N-acetylmannosamine kinase [J].

Hinderlich, S ;

Stasche, R ;

Zeitler, R ;

Reutter, W .

JOURNAL OF BIOLOGICAL CHEMISTRY, 1997, 272 (39) :24313-24318

[7] Alkynyl sugar analogs for the labeling and visualization of glycoconjugates in cells [J].

Hsu, Tsui-Ling ;

Hanson, Sarah R. ;

Kishikawa, Kuniyuki ;

Wang, Sheng-Kai ;

Sawa, Masaaki ;

Wong, Chi-Huey .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2007, 104 (08) :2614-2619

[8] Cell surface glycoproteomic analysis of prostate cancer-derived PC-3 cells [J].

Hubbard, Sarah C. ;

Boyce, Michael ;

McVaugh, Cheryl T. ;

Peehl, Donna M. ;

Bertozzi, Carolyn R. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (17) :4945-4950

[9] Expanding the diversity of unnatural cell-surface sialic acids [J].

Luchansky, SJ ;

Goon, S ;

Bertozzi, CR .

CHEMBIOCHEM, 2004, 5 (03) :371-374

[10] Chemistry in living systems [J].

Prescher, JA ;

Bertozzi, CR .

NATURE CHEMICAL BIOLOGY, 2005, 1 (01) :13-21