Literature DB >> 27623688

Total Synthesis of the Complete Protective Antigen of Vibrio cholerae O139.

Sameh E Soliman1,2, Pavol Kováč3.   

Abstract

The first chemical synthesis of the complete protective O-antigen of a human-disease-causing pathogenic bacterium is described. The synthesis involved a protecting-group strategy that facilitated the regioselectivity of the key transformations, stereoselective glycosylation reactions, and enabled the one-step global deprotection of the completely assembled, fully protected, phosphorylated hexasaccharide by hydrogenation/hydrogenolysis. The final amino-group-functionalized, linker-equipped antigen was obtained in a form ready for conjugation to suitable carriers, for example, proteins, to yield immunogens.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  O-specific antigens; glycosylation; oligosaccharides; pathogenic bacteria; stereoselectivity

Mesh：

Substances：

Year:  2016        PMID： 27623688      PMCID： PMC5165651          DOI： 10.1002/anie.201606116

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  13 in total

1.  Regioselective synthesis of a glycomimetic trisaccharide of Sialyl Lewis (sLex).

Authors:  Sameh E Soliman; Rafik W Bassily; Ramadan I El-Sokkary; Joseph Banoub; Mina A Nashed
Journal:  Carbohydr Res       Date:  2008-12-10       Impact factor: 2.104

2.  Structural analysis of the O-antigen-core region of the lipopolysaccharide from Vibrio cholerae O139.

Authors:  A D Cox; M B Perry
Journal:  Carbohydr Res       Date:  1996-08-26       Impact factor: 2.104

3.  Stereoselective Syntheses of the Conjugation-Ready, Downstream Disaccharide and Phosphorylated Upstream, Branched Trisaccharide Fragments of the O-PS of Vibrio cholerae O139.

Authors:  Sameh E Soliman; Pavol Kováč
Journal:  J Org Chem       Date:  2015-05-04       Impact factor: 4.354

Review 4.  Cholera.

Authors:  J B Kaper; J G Morris; M M Levine
Journal:  Clin Microbiol Rev       Date:  1995-01       Impact factor: 26.132

5.  Large outbreak of clinical cholera due to Vibrio cholerae non-O1 in Bangladesh.

Authors:  M J Albert; A K Siddique; M S Islam; A S Faruque; M Ansaruzzaman; S M Faruque; R B Sack
Journal:  Lancet       Date:  1993-03-13       Impact factor: 79.321

6.  Chromatography on Sephadex LH20 as an efficient purification step after removal of internucleotide 2,2,2-trichloroethyl protective groups from oligoribonucleotide phosphotriesters.

Authors:  K Grześkowiak; R W Adamiak; M Wiewiórowski
Journal:  Nucleic Acids Res       Date:  1980-03-11       Impact factor: 16.971

7.  Induction of protective immunity by synthetic Vibrio cholerae hexasaccharide derived from V. cholerae O1 Ogawa lipopolysaccharide bound to a protein carrier.

Authors:  Anatoly Chernyak; Seiichi Kondo; Terri K Wade; Michael D Meeks; Pedro M Alzari; Jean-Michel Fournier; Ronald K Taylor; Pavol Kovác; William F Wade
Journal:  J Infect Dis       Date:  2002-03-19       Impact factor: 5.226

8.  Study of glycosylation with N-trichloroacetyl-D-glucosamine derivatives in the syntheses of the spacer-armed pentasaccharides sialyl lacto-N-neotetraose and sialyl lacto-N-tetraose, their fragments, and analogues.

Authors:  A A Sherman; O N Yudina; Y V Mironov; E V Sukhova; A S Shashkov; V M Menshov; N E Nifantiev
Journal:  Carbohydr Res       Date:  2001-11-01       Impact factor: 2.104

9.  Further studies on the use of 2,2,2-trichloroethyl groups for phosphate protection in phosphoserine peptide synthesis.

Authors:  A Paquet
Journal:  Int J Pept Protein Res       Date:  1992-01

10.  Transcutaneous immunization with a Vibrio cholerae O1 Ogawa synthetic hexasaccharide conjugate following oral whole-cell cholera vaccination boosts vibriocidal responses and induces protective immunity in mice.

Authors:  A A Tarique; A Kalsy; M Arifuzzaman; S M Rollins; R C Charles; D T Leung; J B Harris; R C Larocque; A Sheikh; M S Bhuiyan; R Saksena; J D Clements; S B Calderwood; F Qadri; P Kovác; E T Ryan
Journal:  Clin Vaccine Immunol       Date:  2012-02-22
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  2 in total

Review 1.  Potential targets for next generation antimicrobial glycoconjugate vaccines.

Authors:  Francesca Micoli; Paolo Costantino; Roberto Adamo
Journal:  FEMS Microbiol Rev       Date:  2018-05-01       Impact factor: 16.408

2.  Defining Polysaccharide-Specific Antibody Targets against Vibrio cholerae O139 in Humans following O139 Cholera and following Vaccination with a Commercial Bivalent Oral Cholera Vaccine, and Evaluation of Conjugate Vaccines Targeting O139.

Authors:  Mohammad Kamruzzaman; Meagan Kelly; Pavol Kováč; Peng Xu; Edward T Ryan; Richelle C Charles; Jason B Harris; Stephen B Calderwood; Aklima Akter; Rajib Biswas; M Hasanul Kaisar; Taufiqur R Bhuiyan; Louise C Ivers; Ralph Ternier; Jean-Gregory Jerome; Hélene B Pfister; Xiaowei Lu; Sameh E Soliman; Bart Ruttens; Rina Saksena; Jana Mečárová; Alžbeta Čížová; Firdausi Qadri; Slavomír Bystrický
Journal:  mSphere       Date:  2021-07-07       Impact factor: 4.389
  2 in total

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