Literature DB >> 33981183

Structure and Reactivity of Glycosyl Isocyanides.

Constantinos G Neochoritis1, Ehsan Ghonchepour1, Maryam Kazemi Miraki1, Tryfon Zarganes-Tzitzikas1, Katarzyna Kurpiewska2, Justyna Kalinowska-Tłuścik2, Alexander Dömling1.   

Abstract

3D structural information was obtained from mono-, di- and trisaccharide formamide and isocyanide derivatives by analysis of their X-ray crystal structure and NMR spectroscopy. The isocyanide anomeric effect was observed. Data mining of the Cambridge Structural Database (CSD) was performed and statistically confirmed our findings. Application of the glycoside isocyanides in the synthesis of novel glycoconjugates as drug-like scaffolds by MCR chemistry underscores the usefulness of the novel building blocks.

Entities:  

Keywords:  Amides; Anomeric effect; Isocyanides; Multicomponent reactions; Oligosaccharides

Year:  2018        PMID： 33981183      PMCID： PMC8112802          DOI： 10.1002/ejoc.201801588

Source DB:  PubMed          Journal:  European J Org Chem        ISSN： 1099-0690


  21 in total

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Journal:  Comb Chem High Throughput Screen       Date:  2002-08       Impact factor: 1.339

2.  Exhaustive fluorine scanning toward potent p53-Mdm2 antagonists.

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3.  Synthesis of multivalent aminoglycoside mimics via the Ugi multicomponent reaction.

Authors:  Bernhard Westermann; Simon Dorner
Journal:  Chem Commun (Camb)       Date:  2005-03-04       Impact factor: 6.222

4.  Ugi-based approaches to quinoxaline libraries.

Authors:  Jhonny Azuaje; Abdelaziz El Maatougui; Xerardo García-Mera; Eddy Sotelo
Journal:  ACS Comb Sci       Date:  2014-05-14       Impact factor: 3.784

5.  An Access to Glycoconjugate Libraries through Multicomponent Reactions.

Authors:  Oswald Lockhoff
Journal:  Angew Chem Int Ed Engl       Date:  1998-12-31       Impact factor: 15.336

6.  Two-Step Synthesis of Complex Artificial Macrocyclic Compounds.

Authors:  Rudrakshula Madhavachary; Eman M M Abdelraheem; Arianna Rossetti; Aleksandra Twarda-Clapa; Bogdan Musielak; Katarzyna Kurpiewska; Justyna Kalinowska-Tłuścik; Tad A Holak; Alexander Dömling
Journal:  Angew Chem Int Ed Engl       Date:  2017-08-01       Impact factor: 15.336

Review 7.  From Oxiranes to Oligomers: Architectures of U.S. FDA Approved Pharmaceuticals Containing Oxygen Heterocycles.

Authors:  Michael D Delost; David T Smith; Benton J Anderson; Jon T Njardarson
Journal:  J Med Chem       Date:  2018-08-01       Impact factor: 7.446

8.  Synthesis of Glycomimetics by Diastereoselective Passerini Reaction.

Authors:  Kristina Vlahoviček-Kahlina; Mario Vazdar; Andreja Jakas; Vilko Smrečki; Ivanka Jerić
Journal:  J Org Chem       Date:  2018-10-24       Impact factor: 4.354

9.  One-Pot Two-Step Multicomponent Process of Indole and Other Nitrogenous Heterocycles or Amines toward α-Oxo-acetamidines.

Authors:  Guillermo Martinez-Ariza; Nicholas McConnell; Christopher Hulme
Journal:  Org Lett       Date:  2016-03-29       Impact factor: 6.005

10.  Conformational analysis of an extracellular polysaccharide produced by Sphaerotilus natans.

Authors:  Keiko Kondo; Minoru Takeda; Tsukasa Mashima; Masato Katahira; Jun-ichi Koizumi; Kazuyoshi Ueda
Journal:  Carbohydr Res       Date:  2012-08-07       Impact factor: 2.104
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