Literature DB >> 12617925

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

Tatsuya Shirahata1, Toshiaki Sunazuka, Kiminari Yoshida, Daisuke Yamamoto, Yoshihiko Harigaya, Takayuki Nagai, Hiroaki Kiyohara, Haruki Yamada, Isao Kuwajima, Satoshi Omura.   

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.

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Year:  2003        PMID: 12617925     DOI: 10.1016/s0960-894x(02)01069-7

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN: 0960-894X            Impact factor:   2.823


  2 in total

1.  An LC-MS/MS workflow to characterize 16 regio- and stereoisomeric trihydroxyoctadecenoic acids.

Authors:  David Fuchs; Mats Hamberg; C Magnus Sköld; Åsa M Wheelock; Craig E Wheelock
Journal:  J Lipid Res       Date:  2018-07-31       Impact factor: 5.922

2.  Steric analysis of epoxyalcohol and trihydroxy derivatives of 9-hydroperoxy-linoleic acid from hematin and enzymatic synthesis.

Authors:  Christopher P Thomas; William E Boeglin; Yoel Garcia-Diaz; Valerie B O'Donnell; Alan R Brash
Journal:  Chem Phys Lipids       Date:  2013-01-23       Impact factor: 3.329

  2 in total

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