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

Carbohydrate Research
N E JacobsenM Powell

Abstract

The saponin QS-21, derived from the bark of the Quillaja saponaria Molina tree, has shown great potential as an adjuvant with a number of vaccines. Kinetic studies carried out to establish the stability of vaccine formulations show that commercially supplied QS-21 (primarily QS-21A) is converted slowly at pH 5.5, and rapidly at higher pH, to an equilibrium mixture of two regioisomers, QS-21A and QS-21B, in a ratio of 20:1. NMR studies show that QS-21A and QS-21B differ only in the point of attachment of the fatty acyl moiety to the fucose sugar ring. The major isomer, QS-21A, has the fatty acyl portion attached at the 4-hydroxyl group whereas the minor isomer, QS-21B, has the fatty acyl portion attached at the 3-hydroxyl group. The isomerization most likely involves ionization of the 3-hydroxy group and intramolecular acyl transfer from the 4-hydroxy group. The relative stereochemistry of the triterpene and the sugar anomeric centers is also established by NMR methods.

References

Dec 16, 1983·Biochemical and Biophysical Research Communications·M RanceK Wüthrich
Aug 12, 1993·Annals of the New York Academy of Sciences·S SoltysikC R Kensil

❮ Previous
Next ❯

Citations

Jun 11, 1998·Phytochemistry·S GuoB G Sundquist
Feb 1, 1997·Mechanisms of Ageing and Development·J J Donnelly
Jun 6, 2000·Advanced Drug Delivery Reviews·J C CoxI G Barr
Mar 16, 2011·Chemical Reviews·Jonas J Forsman, Reko Leino
Jan 22, 2010·Journal of the American Chemical Society·Michelle M AdamsDavid Y Gin
Apr 27, 2007·Nature·Danica P Galonić, David Y Gin
Nov 6, 2004·Nature Biotechnology·Arthur J Chirino, Anthony Mire-Sluis
Feb 27, 2004·Natural Product Research·C KauffmannG Gosmann
Feb 27, 2007·Journal of Zhejiang University. Science. B·Zahid Iqbal RajputAbdullah G Arijo
Aug 21, 2010·Future Medicinal Chemistry·Michael R RonerMelody Kiesling-Barrager
Mar 26, 2014·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Conrado PedebosHugo Verli
Dec 11, 2007·Canadian Journal of Physiology and Pharmacology·Georgios S KatselisBranka Barl
Sep 16, 2015·Expert Opinion on Drug Discovery·Jing HuJian Yin
Nov 6, 2015·Natural Product Research·Long-Xiao XieJing-Yong Sun
Dec 8, 2005·International Immunopharmacology·Hongxiang SunYiping Ye
Oct 6, 2007·Expert Opinion on Biological Therapy·Pieranna ChiarellaVito Michele Fazio
Jul 5, 2005·Expert Opinion on Investigational Drugs·C R Kensil, R Kammer
Jan 1, 1996·Journal of Pharmaceutical Sciences·J L ClelandM F Powell
Feb 12, 2009·Vaccine·Hong-Xiang SunYi-Ping Ye
Oct 27, 2016·Expert Opinion on Therapeutic Patents·Milena MasulloSonia Piacente
Aug 6, 2015·Chemical Communications : Chem Comm·Alberto Fernández-TejadaDavid Y Gin
Nov 26, 2015·International Immunopharmacology·Dante J Marciani
Jun 21, 2014·Nature Chemistry·Alberto Fernández-TejadaDavid Y Gin
Dec 29, 2006·Chemistry & Biodiversity·Hong-Xiang SunYiping Ye
Oct 22, 2010·Chemistry & Biodiversity·Biswanath DindaYoshihiro Harigaya
Jul 16, 2019·Future Medicinal Chemistry·Yve Vs MagedansArthur G Fett-Neto
Nov 5, 2019·Glycobiology·Anam SaqibDitte Hededam Welner
Nov 2, 2004·Rapid Communications in Mass Spectrometry : RCM·Geoffrey C KiteMonique S J Simmonds
Dec 29, 2006·Chemistry & Biodiversity·Hongxiang SunYuanjian Pan
Jan 10, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Juliane Deise FleckSimone Gasparin Verza
Feb 13, 2001·The Journal of Immunology : Official Journal of the American Association of Immunologists·P N BoyakaJ R McGhee

❮ Previous
Next ❯

Related Concepts

Related Feeds

Avian Influenza: Innate Immune Adjuvant (ASM)

Adjuvants systems that are added to vaccines against avian influenza have be explored to enhance the innate immune system response against the virus. Here is the latest research on avian influenza and the innate immune adjuvant.

Avian Influenza: Innate Immune Adjuvant

Adjuvants systems that are added to vaccines against avian influenza have be explored to enhance the innate immune system response against the virus. Here is the latest research on avian influenza and the innate immune adjuvant.