Literature DB >> 29247910

Conjugation of carbohydrates to proteins using di(triethylene glycol monomethyl ether) squaric acid ester revisited.

Peng Xu1, Michael N Trinh1, Pavol Kováč2.   

Abstract

Properties of di(triethylene glycol monomethyl ether) squarate relevant to conjugation of carbohydrates to proteins have been reinvestigated and compared with those of dimethyl squarate. It is concluded that the commercially available, crystalline dimethyl squarate remains the most convenient and efficient reagent for conjugation of amine-containing carbohydrates to proteins by a two-step or one-pot conjugation protocol. Published by Elsevier Ltd.

Entities:  

Keywords:  Glycoconjugates; Hydrolytic stability; Squarate; Squaric acid chemistry

Mesh：

Substances：

Year:  2017        PMID： 29247910      PMCID： PMC5808912          DOI： 10.1016/j.carres.2017.10.012

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


  23 in total

1.  Conjugate Vaccines from Bacterial Antigens by Squaric Acid Chemistry: A Closer Look.

Authors:  Peng Xu; Meagan Kelly; Willie F Vann; Firdausi Qadri; Edward T Ryan; Pavol Kováč
Journal:  Chembiochem       Date:  2017-03-23       Impact factor: 3.164

2.  Synthesis of a globotetraose trimer.

Authors:  Anders Bergh; Sumita Bhattacharyya; Ulf J Nilsson
Journal:  Carbohydr Res       Date:  2002-05-13       Impact factor: 2.104

3.  Synthesis of the Lewis b hexasaccharide and squarate acid-HSA conjugates thereof with various saccharide loadings.

Authors:  A Chernyak; S Oscarson; D Turek
Journal:  Carbohydr Res       Date:  2000-11-03       Impact factor: 2.104

4.  Preparations of antigens and immunoadsorbents corresponding to the Streptococcus group A cell-wall polysaccharide.

Authors:  F I Auzanneau; B M Pinto
Journal:  Bioorg Med Chem       Date:  1996-11       Impact factor: 3.641

5.  Formation of squaric acid amides of anthracycline antibiotics. Synthesis and cytotoxic properties.

Authors:  Anna Tevyashova; Ferenc Sztaricskai; Gyula Batta; Pál Herczegh; András Jeney
Journal:  Bioorg Med Chem Lett       Date:  2004-09-20       Impact factor: 2.823

6.  One-pot preparation of a series of glycoconjugates with predetermined antigen-carrier ratio from oligosaccharides that mimic the O-PS of Vibrio cholerae O:1, serotype Ogawa.

Authors:  Rina Saksena; Xingquan Ma; Pavol Kovác
Journal:  Carbohydr Res       Date:  2003-11-14       Impact factor: 2.104

Review 7.  Be squared: expanding the horizon of squaric acid-mediated conjugations.

Authors:  Frederik R Wurm; Harm-Anton Klok
Journal:  Chem Soc Rev       Date:  2013-07-22       Impact factor: 54.564

8.  Multimeric bivalent immunogens from recombinant tetanus toxin HC fragment, synthetic hexasaccharides, and a glycopeptide adjuvant.

Authors:  Aileen F G Bongat; Rina Saksena; Roberto Adamo; Yukari Fujimoto; Zenyu Shiokawa; Dwight C Peterson; Koichi Fukase; Willie F Vann; Pavol Kovác
Journal:  Glycoconj J       Date:  2009-09-16       Impact factor: 2.916

9.  Immunogens related to the synthetic tetrasaccharide side chain of the Bacillus anthracis exosporium.

Authors:  Rina Saksena; Roberto Adamo; Pavol Kovác
Journal:  Bioorg Med Chem       Date:  2007-03-23       Impact factor: 3.641

10.  Use of diethyl squarate for the coupling of oligosaccharide amines to carrier proteins and characterization of the resulting neoglycoproteins by MALDI-TOF mass spectrometry.

Authors:  V P Kamath; P Diedrich; O Hindsgaul
Journal:  Glycoconj J       Date:  1996-04       Impact factor: 2.916
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  2 in total

1.  Structure-Immunogenicity Relationship of α- and β-Tetrasaccharide Glycoforms from Bacillus anthracis Exosporium and Fragments Thereof.

Authors:  Riccardo De Ricco; Christy L Ventura; Filippo Carboni; Rina Saksena; Pavol Kováč; Roberto Adamo
Journal:  Molecules       Date:  2018-08-20       Impact factor: 4.411

Review 2.  Glycoconjugations of Biomolecules by Chemical Methods.

Authors:  Biswajit Sarkar; Narayanaswamy Jayaraman
Journal:  Front Chem       Date:  2020-11-04       Impact factor: 5.221
  2 in total

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