Literature DB >> 18039537

A convenient synthesis of the C-1-phosphonate analogue of UDP-GlcNAc and its evaluation as an inhibitor of O-linked GlcNAc transferase (OGT).

Jan Hajduch1, Ghilsoo Nam, Eun Ju Kim, Roland Fröhlich, John A Hanover, Kenneth L Kirk.   

Abstract

The C-1-phosphonate analogue of UDP-GlcNAc has been synthesized using an alpha-configured C-1-aldehyde as a key intermediate. Addition of the anion of diethyl phosphate to the aldehyde produced the hydroxyphosphonate. The configuration of this key intermediate was determined by X-ray crystallography. Deoxygenation, coupling of the resulting phosphonic acid with UMP and deprotection gave the target molecule as a di-sodium salt. This analogue had no detectable activity as an inhibitor of (OGT).

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Year:  2007        PMID： 18039537      PMCID： PMC2243073          DOI： 10.1016/j.carres.2007.10.027

Source DB:  PubMed          Journal:  Carbohydr Res        ISSN： 0008-6215            Impact factor:   2.104


  19 in total

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Journal:  J Am Chem Soc       Date:  2001-10-10       Impact factor: 15.419

2.  Multiparametric scaling of diffraction intensities.

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Journal:  Acta Crystallogr A       Date:  2003-04-25       Impact factor: 2.290

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Review 4.  Cell signaling, the essential role of O-GlcNAc!

Authors:  Natasha E Zachara; Gerald W Hart
Journal:  Biochim Biophys Acta       Date:  2006-05-06

5.  Development of co- and post-translational synthetic strategies to C-neoglycopeptides.

Authors:  Glenn J McGarvey; Tyler E Benedum; Frank W Schmidtmann
Journal:  Org Lett       Date:  2002-10-17       Impact factor: 6.005

6.  Synthesis of novel donor mimetics of UDP-Gal, UDP-GlcNAc, and UDP-GalNAc as potential transferase inhibitors.

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Journal:  J Org Chem       Date:  2000-01-14       Impact factor: 4.354

Review 7.  Glycan-dependent signaling: O-linked N-acetylglucosamine.

Authors:  J A Hanover
Journal:  FASEB J       Date:  2001-09       Impact factor: 5.191

8.  1H-Tetrazole as Catalyst in Phosphomorpholidate Coupling Reactions: Efficient Synthesis of GDP-Fucose, GDP-Mannose, and UDP-Galactose.

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Journal:  J Org Chem       Date:  1997-04-04       Impact factor: 4.354

9.  Improved procedure for the oxidative cleavage of olefins by OsO4-NaIO4.

Authors:  Wensheng Yu; Yan Mei; Ying Kang; Zhengmao Hua; Zhendong Jin
Journal:  Org Lett       Date:  2004-09-16       Impact factor: 6.005

10.  Analysis of nuclear pore protein p62 glycosylation.

Authors:  W A Lubas; M Smith; C M Starr; J A Hanover
Journal:  Biochemistry       Date:  1995-02-07       Impact factor: 3.162
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  9 in total

1.  Mechanism, Structure, and Inhibition of O-GlcNAc Processing Enzymes.

Authors:  Tracey M Gloster; David J Vocadlo
Journal:  Curr Signal Transduct Ther       Date:  2010-01

2.  The importance of hydrogen bonding and aromatic stacking to the affinity and efficacy of cannabinoid receptor CB2 antagonist, 5-(4-chloro-3-methylphenyl)-1-[(4-methylphenyl)methyl]-N-[(1S,2S,4R)-1,3,3-trimethylbicyclo[2.2.1]hept-2-yl]-1H-pyrazole-3-carboxamide (SR144528).

Authors:  Evangelia Kotsikorou; Frank Navas; Michael J Roche; Anne F Gilliam; Brian F Thomas; Herbert H Seltzman; Pritesh Kumar; Zhao-Hui Song; Dow P Hurst; Diane L Lynch; Patricia H Reggio
Journal:  J Med Chem       Date:  2013-08-14       Impact factor: 7.446

3.  Molecular recognition in the P2Y(14) receptor: Probing the structurally permissive terminal sugar moiety of uridine-5'-diphosphoglucose.

Authors:  Hyojin Ko; Arijit Das; Rhonda L Carter; Ingrid P Fricks; Yixing Zhou; Andrei A Ivanov; Artem Melman; Bhalchandra V Joshi; Pavol Kovác; Jan Hajduch; Kenneth L Kirk; T Kendall Harden; Kenneth A Jacobson
Journal:  Bioorg Med Chem       Date:  2009-05-15       Impact factor: 3.641

4.  Substrate and product analogues as human O-GlcNAc transferase inhibitors.

Authors:  Helge C Dorfmueller; Vladimir S Borodkin; David E Blair; Shalini Pathak; Iva Navratilova; Daan M F van Aalten
Journal:  Amino Acids       Date:  2010-07-17       Impact factor: 3.520

5.  A neutral diphosphate mimic crosslinks the active site of human O-GlcNAc transferase.

Authors:  Jiaoyang Jiang; Michael B Lazarus; Lincoln Pasquina; Piotr Sliz; Suzanne Walker
Journal:  Nat Chem Biol       Date:  2011-11-13       Impact factor: 15.040

6.  Structural insights into mechanism and specificity of O-GlcNAc transferase.

Authors:  Andrew J Clarke; Ramon Hurtado-Guerrero; Shalini Pathak; Alexander W Schüttelkopf; Vladimir Borodkin; Sharon M Shepherd; Adel F M Ibrahim; Daan M F van Aalten
Journal:  EMBO J       Date:  2008-09-25       Impact factor: 11.598

7.  Structural basis of the molecular ruler mechanism of a bacterial glycosyltransferase.

Authors:  Ana S Ramírez; Jérémy Boilevin; Ahmad Reza Mehdipour; Gerhard Hummer; Tamis Darbre; Jean-Louis Reymond; Kaspar P Locher
Journal:  Nat Commun       Date:  2018-01-31       Impact factor: 14.919

8.  Synthesis and Preliminary Evaluation of Biological Activity of Glycoconjugates Analogues of Acyclic Uridine Derivatives.

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Journal:  Molecules       Date:  2018-08-13       Impact factor: 4.411

9.  Novel Uridine Glycoconjugates, Derivatives of 4-Aminophenyl 1-Thioglycosides, as Potential Antiviral Compounds.

Authors:  Ewelina Krol; Gabriela Pastuch-Gawolek; Binay Chaubey; Gabriela Brzuska; Karol Erfurt; Boguslaw Szewczyk
Journal:  Molecules       Date:  2018-06-13       Impact factor: 4.411
  9 in total

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