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

Citation data:

Organic letters, ISSN: 1523-7052, Vol: 17, Issue: 2, Page: 286-9

Publication Year:
2015
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Citations 13
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PMID:
25534255
DOI:
10.1021/ol5033893
Author(s):
Li, Ke, Huertas, Mar, Brant, Cory, Chung-Davidson, Yu-Wen, Bussy, Ugo, Hoye, Thomas R, Li, Weiming
Publisher(s):
American Chemical Society (ACS)
Tags:
Biochemistry, Genetics and Molecular Biology, Chemistry
article description
(+)- 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.

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