Details of the structure determination of the sulfated steroids PSDS and PADS: New components of the sea lamprey (Petromyzon marinus) migratory pheromone

Thomas R. Hoye, Vadims Dvornikovs, Jared M. Fine, Kari R. Anderson, Christopher S. Jeffrey, David C. Muddiman, Feng Shao, Peter W. Sorensen, Jizhou Wang

Research output: Contribution to journalArticlepeer-review

36 Scopus citations

Abstract

(Chemical Equation Presented) The discovery of two new components of the migratory pheromone used by sea lamprey to guide adults to spawning grounds was recently reported. These hold promise for use in a pheromone-based control program for this species, an invasive pest in the Great Lakes. Details of the structure determination of these steroidal bis-sulfates [petromyzosterol disulfate (PSDS, 2) and petromyzonamine disulfate (PADS, 3)] are described here. Pattern matching of 1H NMR data was particularly valuable. This involved comparison of spectra of the natural samples of 2 and 3 with those of appropriate steroidal analogues [e.g., petromyzonol sulfate (PS, 1, a previously known sea lamprey bile acid derivative that is a third component of the migratory pheromone), cholesterol sulfate (6), and squalamine (8)] and model compounds containing the unprecedented aminolactam substructure present in 3. The logic underlying the iterative analyses used is presented.

Original languageEnglish (US)
Pages (from-to)7544-7550
Number of pages7
JournalJournal of Organic Chemistry
Volume72
Issue number20
DOIs
StatePublished - Sep 28 2007

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