Synthesis and structure verification of the vaccine adjuvant QS-7-Api. Synthetic access to homogeneous Quillaja saponaria immunostimulants

  • J Am Chem Soc. 2008 May 7;130(18):5860-1. doi: 10.1021/ja801008m.
Kai Deng  1 ,  Michelle M Adams ,  David Y Gin
Affiliations
  • 1. Memorial Sloan-Kettering Cancer Center, 1275 York Avenue, New York, New York 10065, USA.
PMID: 18410100 DOI: 10.1021/ja801008m
Abstract

QS-7-Api is an exceedingly potent immuno-adjuvant isolated from the bark of Quillaja saponaria. It is significantly less toxic than QS-21, a related saponin that is currently the favored Adjuvant in Anticancer and Antiviral vaccine clinical trials. Tedious isolation/purification protocols and uncertainty in its structural constitution have hindered the clinical development of QS-7. A chemical synthesis of QS-7-Api is described, providing structural verification of the Adjuvant. A novel semisynthetic sequence to QS-7-Api has also been established, greatly facilitating access to QS-7 for preclinical and clinical evaluation.

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