Literature DB >> 16095333

A new method for conjugation of carbohydrates to proteins using an aminooxy-thiol heterobifunctional linker.

Joanna Kubler-Kielb1, Vince Pozsgay.   

Abstract

A new, efficient, and mild protocol is presented for the coupling of saccharides to proteins. First, a heterobifunctional aminooxy-thiol linker is coupled to the bromoacylated protein to introduce aminooxy groups through thioether linkages. Condensation of the aminooxylated protein and aldehydo/keto-derivatized carbohydrates affords covalent saccharide-protein constructs. Uncoupled saccharide can be recovered in its original form. The scope of our protocol is exemplified by the coupling of neutral mono- and tetrasaccharides and a negatively charged ribitol-phosphate construct to BSA.

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Year:  2005        PMID： 16095333     DOI： 10.1021/jo050934b

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


  12 in total

1.  Synthesis of an experimental glycolipoprotein vaccine against Lyme disease.

Authors:  Vince Pozsgay; Joanna Kubler-Kielb
Journal:  Carbohydr Res       Date:  2006-11-17       Impact factor: 2.104

2.  Toward a new vaccine for pertussis.

Authors:  John B Robbins; Rachel Schneerson; Joanna Kubler-Kielb; Jerry M Keith; Birger Trollfors; Evgeny Vinogradov; Joseph Shiloach
Journal:  Proc Natl Acad Sci U S A       Date:  2014-02-20       Impact factor: 11.205

3.  Immunochemical studies of Shigella flexneri 2a and 6, and Shigella dysenteriae type 1 O-specific polysaccharide-core fragments and their protein conjugates as vaccine candidates.

Authors:  Joanna Kubler-Kielb; Evgeny Vinogradov; Christopher Mocca; Vince Pozsgay; Bruce Coxon; John B Robbins; Rachel Schneerson
Journal:  Carbohydr Res       Date:  2010-05-15       Impact factor: 2.104

4.  Oligosaccharide conjugates of Bordetella pertussis and bronchiseptica induce bactericidal antibodies, an addition to pertussis vaccine.

Authors:  Joanna Kubler-Kielb; Evgeny Vinogradov; Teresa Lagergård; Ariel Ginzberg; Jerry D King; Andrew Preston; Duncan J Maskell; Vince Pozsgay; Jerry M Keith; John B Robbins; Rachel Schneerson
Journal:  Proc Natl Acad Sci U S A       Date:  2011-02-22       Impact factor: 11.205

5.  Synthetic oligosaccharides as tools to demonstrate cross-reactivity between polysaccharide antigens.

Authors:  Vince Pozsgay; Joanna Kubler-Kielb; Bruce Coxon; Paul Santacroce; John B Robbins; Rachel Schneerson
Journal:  J Org Chem       Date:  2012-06-29       Impact factor: 4.354

6.  Saccharide/protein conjugate vaccines for Bordetella species: preparation of saccharide, development of new conjugation procedures, and physico-chemical and immunological characterization of the conjugates.

Authors:  Joanna Kubler-Kielb; Evgeny Vinogradov; Gil Ben-Menachem; Vince Pozsgay; John B Robbins; Rachel Schneerson
Journal:  Vaccine       Date:  2008-05-20       Impact factor: 3.641

7.  Allylic selenosulfide rearrangement: a method for chemical ligation to cysteine and other thiols.

Authors:  David Crich; Venkataramanan Krishnamurthy; Thomas K Hutton
Journal:  J Am Chem Soc       Date:  2006-03-01       Impact factor: 15.419

8.  Effect of the nonreducing end of Shigella dysenteriae type 1 O-specific oligosaccharides on their immunogenicity as conjugates in mice.

Authors:  Vince Pozsgay; Joanna Kubler-Kielb; Rachel Schneerson; John B Robbins
Journal:  Proc Natl Acad Sci U S A       Date:  2007-08-28       Impact factor: 11.205

9.  Adapter reagents for protein site specific dye labeling.

Authors:  Darren A Thompson; Eric G B Evans; Tomas Kasza; Glenn L Millhauser; Philip E Dawson
Journal:  Biopolymers       Date:  2014-05       Impact factor: 2.505

10.  Facile preparation of fluorescent neoglycoproteins using p-nitrophenyl anthranilate as a heterobifunctional linker.

Authors:  Anthony Luyai; Yi Lasanajak; David F Smith; Richard D Cummings; Xuezheng Song
Journal:  Bioconjug Chem       Date:  2009-07-22       Impact factor: 4.774
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