Literature DB >> 18991380

Synthesis of sugar nucleotides by application of phosphoramidites.

Henrik Gold1, Pieter van Delft, Nico Meeuwenoord, Jeroen D C Codée, Dmitri V Filippov, Gerrit Eggink, Herman S Overkleeft, Gijs A van der Marel.   

Abstract

A new method for the construction of pyrophosphates is reported based on the coupling of a sugar phosphate and a nucleoside phosphoramidite. The in situ formed phosphate-phosphite intermediate was subsequently oxidized with tBuOOH. Three UDP-N-acetylglucosamine derivatives were prepared using this one-pot procedure in good yields.

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Year:  2008        PMID： 18991380     DOI： 10.1021/jo802021t

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  7 in total

1.  Chemoenzymatic syntheses and anti-HIV-1 activity of glucose-nucleoside conjugates as prodrugs.

Authors:  Tatiana Rodríguez-Pérez; Susana Fernández; Yogesh S Sanghvi; Mervi Detorio; Raymond F Schinazi; Vicente Gotor; Miguel Ferrero
Journal:  Bioconjug Chem       Date:  2010-11-15       Impact factor: 4.774

2.  Mimetics of ADP-Ribosylated Histidine through Copper(I)-Catalyzed Click Chemistry.

Authors:  Hugo Minnee; Johannes G M Rack; Gijsbert A van der Marel; Herman S Overkleeft; Jeroen D C Codée; Ivan Ahel; Dmitri V Filippov
Journal:  Org Lett       Date:  2022-05-19       Impact factor: 6.072

3.  Molecular Tools for the Study of ADP-Ribosylation: A Unified and Versatile Method to Synthesise Native Mono-ADP-Ribosylated Peptides.

Authors:  Jim Voorneveld; Johannes Gregor Matthias Rack; Luke van Gijlswijk; Nico J Meeuwenoord; Qiang Liu; Herman S Overkleeft; Gijsbert A van der Marel; Ivan Ahel; Dmitri V Filippov
Journal:  Chemistry       Date:  2021-05-06       Impact factor: 5.020

4.  Studies on the substrate specificity of a GDP-mannose pyrophosphorylase from Salmonella enterica.

Authors:  Lu Zou; Ruixiang Blake Zheng; Todd L Lowary
Journal:  Beilstein J Org Chem       Date:  2012-08-01       Impact factor: 2.883

Review 5.  Synthesis of selected unnatural sugar nucleotides for biotechnological applications.

Authors:  Meng Qiao; Bingzhi Li; Yuan Ji; Lei Lin; Robert Linhardt; Xing Zhang
Journal:  Crit Rev Biotechnol       Date:  2020-11-05       Impact factor: 8.429

6.  O-GlcNAc transferase invokes nucleotide sugar pyrophosphate participation in catalysis.

Authors:  Marianne Schimpl; Xiaowei Zheng; Vladimir S Borodkin; David E Blair; Andrew T Ferenbach; Alexander W Schüttelkopf; Iva Navratilova; Tonia Aristotelous; Osama Albarbarawi; David A Robinson; Megan A Macnaughtan; Daan M F van Aalten
Journal:  Nat Chem Biol       Date:  2012-10-28       Impact factor: 15.040

7.  Mechanistic insights into the three steps of poly(ADP-ribosylation) reversal.

Authors:  Johannes Gregor Matthias Rack; Qiang Liu; Valentina Zorzini; Jim Voorneveld; Antonio Ariza; Kourosh Honarmand Ebrahimi; Julia M Reber; Sarah C Krassnig; Dragana Ahel; Gijsbert A van der Marel; Aswin Mangerich; James S O McCullagh; Dmitri V Filippov; Ivan Ahel
Journal:  Nat Commun       Date:  2021-07-28       Impact factor: 14.919
  7 in total

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