(+)- and (-)-petromyroxols: Antipodal tetrahydrofurandiols from larval sea lamprey (petromyzon marinus L.) that elicit enantioselective olfactory responses

Ke Li, Mar Huertas, Cory Brant, Yu Wen Chung-Davidson, Ugo Bussy, Thomas R Hoye, Weiming Li

Research output: Contribution to journalArticlepeer-review

19 Scopus citations

Abstract

(+)- and (-)-Petromyroxol [(+)-1 and (-)-1, respectively], two novel tetrahydrofuran (THF)-diol fatty acid enantiomers, were isolated from water conditioned with larval sea lamprey. We herein describe their isolation and subsequent resolution using chiral chromatography. The absolute configuration of each enantiomer was determined by a combination of Mosher ester analysis and comparison with related natural and synthetic products. Electro-olfactogram (EOG) assays indicated that (+)-petromyroxol (1) possesses potent olfactory activity for sea lamprey.

Original languageEnglish (US)
Pages (from-to)286-289
Number of pages4
JournalOrganic Letters
Volume17
Issue number2
DOIs
StatePublished - Jan 16 2015

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