Total synthesis and adjuvant activity of all stereoisomers of pinellic acid.

Abstract

Pinellic acid is a novel and potentially useful oral adjuvant when used in conjunction with intranasal inoculation of influenza HA vaccines. All stereoisomers of pinellic acid have been synthesized via regioselective asymmetric dihydroxylation, regioselective inversion, and stereoselective reduction, and their adjuvant activities were characterized. Among this series of isomers, 9S, 12S, 13S compound has the most potent adjuvant activity. Structure-activity relationships are discussed.

• Authors: Tatsuya Shirahata, Toshiaki Sunazuka, Kiminari Yoshida, Daisuke Yamamoto, Yoshihiko Harigaya, Takayuki Nagai, Hiroaki Kiyohara, Haruki Yamada, Isao Kuwajima, Satoshi Omura
• Journal: Bioorganic & medicinal chemistry letters (Bioorg Med Chem Lett) Vol. 13 Issue 5 Pg. 937-41 (Mar 10 2003) ISSN: 0960-894X [Print] England
• PMID: 12617925 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Adjuvants, Immunologic
• Antibodies, Viral
• Fatty Acids, Unsaturated
• Immunoglobulin A
• Immunoglobulin G
• pinellic acid

Topics

• Adjuvants, Immunologic (chemistry, pharmacology)
• Animals
• Antibodies, Viral (blood)
• Fatty Acids, Unsaturated (chemistry, pharmacology)
• Hydroxylation
• Immunoglobulin A (blood)
• Immunoglobulin G (blood)
• Mice
• Orthomyxoviridae (drug effects, immunology)
• Oxidation-Reduction
• Pinellia (chemistry)
• Stereoisomerism
• Structure-Activity Relationship