title: Synthesis of a phostone glycomimetic of the endothelin converting enzyme inhibitor phosphoramidon.
abstract: The phostone analog of phosphoramidon, an inhibitor of endothelin converting enzyme, was synthesized from L-rhamnose. Coupling of the cyclic phosphonic acid with the dipeptide H-Leu-Trp-OMe gave, after deprotection and purification by reverse-phase HPLC, the desired phostone which exhibited an IC50 of 5.05+/-2.7 microM.
authors.affiliation: Department of Chemistry, Université de Montréal, Canada.
authors.forename: S
authors.initials: S
authors.lastname: Hanessian
authors.forename: O
authors.initials: O
authors.lastname: Rogel
mesh_terms: D016282:Aspartic Acid Endopeptidases / Q000037:antagonists & inhibitors*; D000072396:Endothelin-Converting Enzymes; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D006020:Glycopeptides / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry / Q000379:methods; D008666:Metalloendopeptidases; D018716:Molecular Mimicry; D015394:Molecular Structure
chemical_list: D004791:Enzyme Inhibitors; D006020:Glycopeptides; D016282:Aspartic Acid Endopeptidases; D008666:Metalloendopeptidases; D000072396:Endothelin-Converting Enzymes; C008890:phosphoramidon