Literature DB >> 23235740

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

Leslie A Bateman1, Balyn W Zaro, Kelly N Chuh, Matthew R Pratt.   

Abstract

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.

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Year:  2012        PMID： 23235740      PMCID： PMC6223258          DOI： 10.1039/c2cc37963e

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  21 in total

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Review 2.  Chemistry in living systems.

Authors:  Jennifer A Prescher; Carolyn R Bertozzi
Journal:  Nat Chem Biol       Date:  2005-06       Impact factor: 15.040

3.  Propargyloxycarbonyl (Poc) as a protective group for the hydroxyl function in carbohydrate synthesis.

Authors:  Perali Ramu Sridhar; S Chandrasekaran
Journal:  Org Lett       Date:  2002-12-26       Impact factor: 6.005

4.  Chemoselective attachment of small molecule effector functionality to human adenoviruses facilitates gene delivery to cancer cells.

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5.  Robust in-gel fluorescence detection of mucin-type O-linked glycosylation.

Authors:  Balyn W Zaro; Leslie A Bateman; Matthew R Pratt
Journal:  Bioorg Med Chem Lett       Date:  2011-04-14       Impact factor: 2.823

6.  Cell surface engineering by a modified Staudinger reaction.

Authors:  E Saxon; C R Bertozzi
Journal:  Science       Date:  2000-03-17       Impact factor: 47.728

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

Authors:  Tsui-Ling Hsu; Sarah R Hanson; Kuniyuki Kishikawa; Sheng-Kai Wang; Masaaki Sawa; Chi-Huey Wong
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8.  Metabolic cross-talk allows labeling of O-linked beta-N-acetylglucosamine-modified proteins via the N-acetylgalactosamine salvage pathway.

Authors:  Michael Boyce; Isaac S Carrico; Anjali S Ganguli; Seok-Ho Yu; Matthew J Hangauer; Sarah C Hubbard; Jennifer J Kohler; Carolyn R Bertozzi
Journal:  Proc Natl Acad Sci U S A       Date:  2011-02-07       Impact factor: 11.205

9.  A chemical approach for identifying O-GlcNAc-modified proteins in cells.

Authors:  David J Vocadlo; Howard C Hang; Eun-Ju Kim; John A Hanover; Carolyn R Bertozzi
Journal:  Proc Natl Acad Sci U S A       Date:  2003-07-21       Impact factor: 11.205

Review 10.  Characterizing glycosylation pathways.

Authors:  K J Yarema; C R Bertozzi
Journal:  Genome Biol       Date:  2001-05-01       Impact factor: 13.583
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  10 in total

1.  The Small Molecule 2-Azido-2-deoxy-glucose Is a Metabolic Chemical Reporter of O-GlcNAc Modifications in Mammalian Cells, Revealing an Unexpected Promiscuity of O-GlcNAc Transferase.

Authors:  Balyn W Zaro; Anna R Batt; Kelly N Chuh; Marisol X Navarro; Matthew R Pratt
Journal:  ACS Chem Biol       Date:  2017-01-30       Impact factor: 5.100

2.  Metabolic Chemical Reporters of Glycans Exhibit Cell-Type-Selective Metabolism and Glycoprotein Labeling.

Authors:  Anna R Batt; Balyn W Zaro; Marisol X Navarro; Matthew R Pratt
Journal:  Chembiochem       Date:  2017-03-28       Impact factor: 3.164

Review 3.  Chemistry-enabled methods for the visualization of cell-surface glycoproteins in Metazoans.

Authors:  Kelly N Chuh; Matthew R Pratt
Journal:  Glycoconj J       Date:  2015-04-28       Impact factor: 2.916

Review 4.  Advances in cell surface glycoengineering reveal biological function.

Authors:  Nicole Nischan; Jennifer J Kohler
Journal:  Glycobiology       Date:  2016-04-10       Impact factor: 4.313

5.  The Metabolic Chemical Reporter 6-Azido-6-deoxy-glucose Further Reveals the Substrate Promiscuity of O-GlcNAc Transferase and Catalyzes the Discovery of Intracellular Protein Modification by O-Glucose.

Authors:  Narek Darabedian; Jinxu Gao; Kelly N Chuh; Christina M Woo; Matthew R Pratt
Journal:  J Am Chem Soc       Date:  2018-05-30       Impact factor: 15.419

6.  Enhanced transfer of a photocross-linking N-acetylglucosamine (GlcNAc) analog by an O-GlcNAc transferase mutant with converted substrate specificity.

Authors:  Andrea C Rodriguez; Seok-Ho Yu; Bin Li; Hicham Zegzouti; Jennifer J Kohler
Journal:  J Biol Chem       Date:  2015-08-03       Impact factor: 5.157

7.  Changes in metabolic chemical reporter structure yield a selective probe of O-GlcNAc modification.

Authors:  Kelly N Chuh; Balyn W Zaro; Friedrich Piller; Véronique Piller; Matthew R Pratt
Journal:  J Am Chem Soc       Date:  2014-08-25       Impact factor: 15.419

8.  Expanding the scope of cyclopropene reporters for the detection of metabolically engineered glycoproteins by Diels-Alder reactions.

Authors:  Anne-Katrin Späte; Verena F Schart; Julia Häfner; Andrea Niederwieser; Thomas U Mayer; Valentin Wittmann
Journal:  Beilstein J Org Chem       Date:  2014-09-22       Impact factor: 2.883

9.  Metabolic precision labeling enables selective probing of O-linked N-acetylgalactosamine glycosylation.

Authors:  Marjoke F Debets; Omur Y Tastan; Simon P Wisnovsky; Stacy A Malaker; Nikolaos Angelis; Leonhard K R Moeckl; Junwon Choi; Helen Flynn; Lauren J S Wagner; Ganka Bineva-Todd; Aristotelis Antonopoulos; Anna Cioce; William M Browne; Zhen Li; David C Briggs; Holly L Douglas; Gaelen T Hess; Anthony J Agbay; Chloe Roustan; Svend Kjaer; Stuart M Haslam; Ambrosius P Snijders; Michael C Bassik; W E Moerner; Vivian S W Li; Carolyn R Bertozzi; Benjamin Schumann
Journal:  Proc Natl Acad Sci U S A       Date:  2020-09-28       Impact factor: 11.205

10.  Design and Synthesis of Metabolic Chemical Reporters for the Visualization and Identification of Glycoproteins.

Authors:  Nichole J Pedowitz; Matthew R Pratt
Journal:  RSC Chem Biol       Date:  2021-02-18
  10 in total

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