title: Details of the structure determination of the sulfated steroids PSDS and PADS: new components of the sea lamprey (petromyzon marinus) migratory pheromone.
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.
authors: Department of Chemistry, 207 Pleasant Street, SE, University of Minnesota, Minneapolis, Minnesota 55455, USA. hoye@chem.umn.edu
authors: Thomas R
authors: TR
authors: Hoye
authors: Vadims
authors: V
authors: Dvornikovs
authors: Jared M
authors: JM
authors: Fine
authors: Kari R
authors: KR
authors: Anderson
authors: Christopher S
authors: CS
authors: Jeffrey
authors: David C
authors: DC
authors: Muddiman
authors: Feng
authors: F
authors: Shao
authors: Peter W
authors: PW
authors: Sorensen
authors: Jizhou
authors: J
authors: Wang
mesh_terms: D000818:Animals; D002776:Cholestanes / Q000737:chemistry*; D008968:Molecular Conformation; D019906:Nuclear Magnetic Resonance, Biomolecular; D048428:Petromyzon / Q000378:metabolism*; D010675:Pheromones / Q000737:chemistry*; D011760:Pyrrolidinones / Q000737:chemistry*
chemical_list: D002776:Cholestanes; D010675:Pheromones; D011760:Pyrrolidinones; C507613:petromyzonamine disulfate; C507614:petromyzosterol disulfate