J. Am. Chem. Soc., 127 (10), 3256 -3257, 2005. 10.1021/ja0422007 S0002-7863(04)02200-0
Web Release Date: February 18, 2005

Copyright © 2005 American Chemical Society

Synthesis of the Potent Immunostimulatory Adjuvant QS-21A

Pengfei Wang, Yong-Jae Kim, Mauricio Navarro-Villalobos, Bridget D. Rohde, and David Y. Gin*

Department of Chemistry, University of Illinois, Urbana, Illinois 61801

gin@scs.uiuc.edu

Received December 27, 2004

Abstract:

QS-21A is one of the most promising new adjuvants for immune response potentiation and dose-sparing in vaccine therapy, given its exceedingly high level of potency and its favorable toxicity profile. Melanoma, breast cancer, small cell lung cancer, prostate cancer, HIV-1, and malaria are among the numerous maladies targeted in more than 80 recent and ongoing clinical trials involving QS-21A as a critical component for immune response augmentation in microgram doses. Herein is reported the first synthesis and structure verification of QS-21Aapi, applying novel glycosylation methodologies in the convergent modular construction of this rare and potent natural product immunostimulant.

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