| Title: | Details of the structure determination of the sulfated steroids PSDS and PADS: new components of the sea lamprey (petromyzon marinus) migratory pheromone |
| Author(s): | Hoye TR; Dvornikovs V; Fine JM; Anderson KR; Jeffrey CS; Muddiman DC; Shao F; Sorensen PW; Wang J; |
| Address: | "Department of Chemistry, 207 Pleasant Street, SE, University of Minnesota, Minneapolis, Minnesota 55455, USA. hoye@chem.umn.edu" |
| ISSN/ISBN: | 0022-3263 (Print) 0022-3263 (Linking) |
| Abstract: | "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" |
| Keywords: | "Animals Cholestanes/*chemistry Molecular Conformation Nuclear Magnetic Resonance, Biomolecular Petromyzon/*metabolism Pheromones/*chemistry Pyrrolidinones/*chemistry;" |
| Notes: | "MedlineHoye, Thomas R Dvornikovs, Vadims Fine, Jared M Anderson, Kari R Jeffrey, Christopher S Muddiman, David C Shao, Feng Sorensen, Peter W Wang, Jizhou eng CA76497/CA/NCI NIH HHS/ GM65597/GM/NIGMS NIH HHS/ Research Support, N.I.H., Extramural Research Support, Non-U.S. Gov't 2007/08/28 J Org Chem. 2007 Sep 28; 72(20):7544-50. doi: 10.1021/jo070957l. Epub 2007 Aug 24" |
