Synthesis and structure verification of the vaccine adjuvant QS-7-Api. Synthetic access to homogeneous Quillaja saponaria immunostimulants Journal Article
| Authors: | Deng, K.; Adams, M. M.; Gin, D. Y. |
| Article Title: | Synthesis and structure verification of the vaccine adjuvant QS-7-Api. Synthetic access to homogeneous Quillaja saponaria immunostimulants |
| 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.Copyright © 2008 American Chemical Society. |
| Keywords: | analytic method; drug structure; drug synthesis; molecular sequence data; glycosylation; immunological adjuvant; plant extract; plant extracts; alkylation; adjuvants, immunologic; structure analysis; carbohydrate sequence; acetylation; saponins; oligosaccharides; quillaja; silylation; quillaja saponaria extract; quillaja saponaria; debenzylation; plant bark |
| Journal Title: | Journal of the American Chemical Society |
| Volume: | 130 |
| Issue: | 18 |
| ISSN: | 0002-7863 |
| Publisher: | American Chemical Society |
| Date Published: | 2008-01-01 |
| Start Page: | 5860 |
| End Page: | 5861 |
| Language: | English |
| DOI: | 10.1021/ja801008m |
| PUBMED: | 18410100 |
| PROVIDER: | scopus |
| PMCID: | PMC2610460 |
| DOI/URL: | |
| Notes: | --- - "Cited By (since 1996): 8" - "Export Date: 17 November 2011" - "CODEN: JACSA" - "Source: Scopus" |
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