Literature DB >> 12227746

A method for bioconjugation of carbohydrates using Diels-Alder cycloaddition.

Vince Pozsgay1, Nancy E Vieira, Alfred Yergey.   

Abstract

Diels-Alder-type cycloaddition of an electronically matched pair of saccharide-linked conjugated dienes and a dienophile-equipped protein gives neoglycoproteins at ambient temperature in pure water with a reaction half-life of approximately 2 h. Uncoupled saccharides can be recovered by diafiltration with complete conservation of the diene moiety, thus allowing their repeated use. The procedure described is the first for creating a carbon-carbon covalent bond in the bioconjugation step between a saccharide and a protein.

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Year:  2002        PMID: 12227746     DOI: 10.1021/ol026179v

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  7 in total

1.  Chemoselective immobilization of biomolecules through aqueous Diels-Alder and PEG chemistry.

Authors:  Xue-Long Sun; Liuchun Yang; Elliot L Chaikof
Journal:  Tetrahedron Lett       Date:  2008       Impact factor: 2.415

Review 2.  Site-selective orientated immobilization of antibodies and conjugates for immunodiagnostics development.

Authors:  Min Shen; Chandra K Dixit; James Rusling
Journal:  Methods       Date:  2016-11-19       Impact factor: 3.608

3.  The Diels-Alder-reaction with inverse-electron-demand, a very efficient versatile click-reaction concept for proper ligation of variable molecular partners.

Authors:  Manfred Wiessler; Waldemar Waldeck; Christian Kliem; Ruediger Pipkorn; Klaus Braun
Journal:  Int J Med Sci       Date:  2009-12-05       Impact factor: 3.738

4.  Novel proteoglycan glycotechnology: chemoenzymatic synthesis of chondroitin sulfate-containing molecules and its application.

Authors:  Masanori Yamaguchi; Keiichi Takagaki; Kaoru Kojima; Naohiro Hayashi; Fengchao Chen; Ikuko Kakizaki; Atsushi Kon; Masahiko Endo
Journal:  Glycoconj J       Date:  2009-07-09       Impact factor: 2.916

5.  Protein glycoengineering enabled by the versatile synthesis of aminooxy glycans and the genetically encoded aldehyde tag.

Authors:  Jason E Hudak; Helen H Yu; Carolyn R Bertozzi
Journal:  J Am Chem Soc       Date:  2011-09-14       Impact factor: 15.419

6.  Gelatin-Based Hydrogels through Homobifunctional Triazolinediones Targeting Tyrosine Residues.

Authors:  Roberto Guizzardi; Luca Vaghi; Marcello Marelli; Antonino Natalello; Ivan Andreosso; Antonio Papagni; Laura Cipolla
Journal:  Molecules       Date:  2019-02-07       Impact factor: 4.411

7.  Diels-Alder cycloadditions in water for the straightforward preparation of peptide-oligonucleotide conjugates.

Authors:  Vicente Marchán; Samuel Ortega; Daniel Pulido; Enrique Pedroso; Anna Grandas
Journal:  Nucleic Acids Res       Date:  2006-02-14       Impact factor: 16.971

  7 in total

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