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Details of the Structure Determination of the Sulfated Steroids PSDS and PADS:  New Components of the Sea Lamprey (Petromyzon marinus) Migratory Pheromone

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journal contribution
posted on 28.09.2007 by Thomas R. Hoye, Vadims Dvornikovs, Jared M. Fine, Kari R. Anderson, Christopher S. Jeffrey, David C. Muddiman, Feng Shao, Peter W. Sorensen, Jizhou Wang
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.