Synthesis of the potent immunostimulatory adjuvant QS-21A.
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.
Wang
Pengfei
P
Department of Chemistry, University of Illinois, Urbana, Illinois 61801, USA.
Kim
Yong-Jae
YJ
Navarro-Villalobos
Mauricio
M
Rohde
Bridget D
BD
Gin
David Y
DY
D000276:Adjuvants, Immunologic / Q000138:chemical synthesis* / Q000737:chemistry; D031990:Quillaja / Q000737:chemistry; D012503:Saponins / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism
D000276:Adjuvants, Immunologic; D012503:Saponins; C078785:saponin QA-21V1