Literature DB >> 26243268

Versatile strategy for the divergent synthesis of linear oligosaccharide domain variants of Quillaja saponin vaccine adjuvants.

Alberto Fernández-Tejada1, Derek S Tan, David Y Gin.   

Abstract

We describe a new, versatile synthetic approach to Quillaja saponin variants based on the natural product immunoadjuvant QS-21. This modular, divergent strategy provides efficient access to linear oligosaccharide domain variants with modified sugars and regiochemistries. This new synthetic approach opens the door to the rapid generation of diverse analogues to identify novel saponin adjuvants with improved synthetic accessibility.

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Year:  2015        PMID： 26243268      PMCID： PMC4643164          DOI： 10.1039/c5cc05244k

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  21 in total

1.  Preparation and characterisation of quillaja saponin with less heterogeneity than Quil-A.

Authors:  S Kamstrup; R San Martin; A Doberti; H Grande; K Dalsgaard
Journal:  Vaccine       Date:  2000-04-28       Impact factor: 3.641

2.  4th meeting on Novel Adjuvants Currently in/close to Human Clinical Testing World Health Organization -- organisation Mondiale de la Santé Fondation Mérieux, Annecy, France, 23-25, June 2003.

Authors:  J Richard Pink; Marie-Paule Kieny
Journal:  Vaccine       Date:  2004-06-02       Impact factor: 3.641

3.  Large-scale chemical and chemo-enzymatic synthesis of a spacer-containing Pk-trisaccharide.

Authors:  Vivekanand P Kamath; Robert E Yeske; Jonathan M Gregson; R Murray Ratcliffe; Ying R Fang; Monica M Palcic
Journal:  Carbohydr Res       Date:  2004-04-28       Impact factor: 2.104

4.  Synthesis of the potent immunostimulatory adjuvant QS-21A.

Authors:  Pengfei Wang; Yong-Jae Kim; Mauricio Navarro-Villalobos; Bridget D Rohde; David Y Gin
Journal:  J Am Chem Soc       Date:  2005-03-16       Impact factor: 15.419

5.  Isomerization and formulation stability of the vaccine adjuvant QS-21.

Authors:  J L Cleland; C R Kensil; A Lim; N E Jacobsen; L Basa; M Spellman; D A Wheeler; J Y Wu; M F Powell
Journal:  J Pharm Sci       Date:  1996-01       Impact factor: 3.534

6.  Comparison of the effect of different immunological adjuvants on the antibody and T-cell response to immunization with MUC1-KLH and GD3-KLH conjugate cancer vaccines.

Authors:  S K Kim; G Ragupathi; C Musselli; S J Choi; Y S Park; P O Livingston
Journal:  Vaccine       Date:  1999-11-12       Impact factor: 3.641

7.  Adjuvant activity of QS-21 isomers.

Authors:  S Soltysik; D A Bedore; C R Kensil
Journal:  Ann N Y Acad Sci       Date:  1993-08-12       Impact factor: 5.691

8.  Structure of the saponin adjuvant QS-21 and its base-catalyzed isomerization product by 1H and natural abundance 13C NMR spectroscopy.

Authors:  N E Jacobsen; W J Fairbrother; C R Kensil; A Lim; D A Wheeler; M F Powell
Journal:  Carbohydr Res       Date:  1996-01-04       Impact factor: 2.104

9.  Total synthesis of lobatoside E, a potent antitumor cyclic triterpene saponin.

Authors:  Chunsheng Zhu; Pingping Tang; Biao Yu
Journal:  J Am Chem Soc       Date:  2008-04-12       Impact factor: 15.419

10.  Separation and characterization of saponins with adjuvant activity from Quillaja saponaria Molina cortex.

Authors:  C R Kensil; U Patel; M Lennick; D Marciani
Journal:  J Immunol       Date:  1991-01-15       Impact factor: 5.422
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  4 in total

1.  Novel Oxime-Derivatized Synthetic Triterpene Glycosides as Potent Saponin Vaccine Adjuvants.

Authors:  Roberto Fuentes; Leire Aguinagalde; Carlo Pifferi; Adrián Plata; Nagore Sacristán; Donatello Castellana; Juan Anguita; Alberto Fernández-Tejada
Journal:  Front Immunol       Date:  2022-05-06       Impact factor: 8.786

2.  Semisynthesis of Analogues of the Saponin Immunoadjuvant QS-21.

Authors:  Alberto Fernández-Tejada; William E Walkowicz; Derek S Tan; David Y Gin
Journal:  Methods Mol Biol       Date:  2017

3.  Design, synthesis, and initial immunological evaluation of glycoconjugates based on saponin adjuvants and the Tn antigen.

Authors:  Roberto Fuentes; Leire Aguinagalde; Nagore Sacristán; Alberto Fernández-Tejada
Journal:  Chem Commun (Camb)       Date:  2021-10-28       Impact factor: 6.222

4.  Development of Improved Vaccine Adjuvants Based on the Saponin Natural Product QS-21 through Chemical Synthesis.

Authors:  Alberto Fernández-Tejada; Derek S Tan; David Y Gin
Journal:  Acc Chem Res       Date:  2016-08-28       Impact factor: 22.384
  4 in total

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