Literature DB >> 17464957

Triazole: the keystone in glycosylated molecular architectures constructed by a click reaction.

Alessandro Dondoni1.   

Abstract

The copper(I)-catalyzed modern version of the Huisgen-type azide-alkyne cycloaddition to give a 1,4-disubstituted 1,2,3-triazole unit is introduced as a powerful ligation method for glycoconjugation. Owing to its high chemoselectivity and tolerance of a variety of reaction conditions, this highly atom-economic and efficient coupling reaction is especially useful for the effective construction of complex glycosylated structures such as clusters, dendrimers, polymers, peptides, and macrocycles. In all cases the triazole ring plays a key role by locking into position the various parts of these molecular architectures. The examples reported and briefly discussed in this short review highlight the use of this reaction in carbohydrate chemistry and pave the way to further developments and applications.

Entities:  

Year:  2007        PMID: 17464957     DOI: 10.1002/asia.200700015

Source DB:  PubMed          Journal:  Chem Asian J        ISSN: 1861-471X


  15 in total

1.  Protecting group-free glycoligation by the desulfurative rearrangement of allylic disulfides as a means of assembly of oligosaccharide mimetics.

Authors:  Venkataraman Subramanian; Myriame Moumé-Pymbock; Tianshun Hu; David Crich
Journal:  J Org Chem       Date:  2011-03-23       Impact factor: 4.354

Review 2.  Transition metal-mediated synthesis of monocyclic aromatic heterocycles.

Authors:  Anton V Gulevich; Alexander S Dudnik; Natalia Chernyak; Vladimir Gevorgyan
Journal:  Chem Rev       Date:  2013-01-10       Impact factor: 60.622

3.  Phenylthiomethyl glycosides: convenient synthons for the formation of azidomethyl and glycosylmethyl glycosides and their derivatives.

Authors:  David Crich; Fan Yang
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

4.  Synthesis and Biological Evaluation of Non-Hydrolizable 1,2,3-Triazole Linked Sialic Acid Derivatives as Neuraminidase Inhibitors.

Authors:  Michel Weïwer; Chi-Chang Chen; Melissa M Kemp; Robert J Linhardt
Journal:  European J Org Chem       Date:  2009-06

5.  Design, synthesis, and anti-tobacco mosaic virus (TMV) activity of glycoconjugates of phenanthroindolizidines alkaloids.

Authors:  Meng Wu; Guifang Han; Chuisong Meng; Ziwen Wang; Yuxiu Liu; Qingmin Wang
Journal:  Mol Divers       Date:  2013-10-17       Impact factor: 2.943

6.  Significant rate accelerated synthesis of glycosyl azides and glycosyl 1,2,3-triazole conjugates.

Authors:  Rishi Kumar; Prakas R Maulik; Anup Kumar Misra
Journal:  Glycoconj J       Date:  2007-12-18       Impact factor: 2.916

Review 7.  Carbohydrate microarrays.

Authors:  Sungjin Park; Jeffrey C Gildersleeve; Ola Blixt; Injae Shin
Journal:  Chem Soc Rev       Date:  2012-11-28       Impact factor: 54.564

8.  Synthesis of heteroglycoclusters by using orthogonal chemoselective ligations.

Authors:  Baptiste Thomas; Michele Fiore; Isabelle Bossu; Pascal Dumy; Olivier Renaudet
Journal:  Beilstein J Org Chem       Date:  2012-03-20       Impact factor: 2.883

9.  Bioorthogonal chemistry: fishing for selectivity in a sea of functionality.

Authors:  Ellen M Sletten; Carolyn R Bertozzi
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

10.  Copper-catalyzed CuAAC/intramolecular C-H arylation sequence: Synthesis of annulated 1,2,3-triazoles.

Authors:  Rajkumar Jeyachandran; Harish Kumar Potukuchi; Lutz Ackermann
Journal:  Beilstein J Org Chem       Date:  2012-10-16       Impact factor: 2.883

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