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