title: Biosynthesis of pyrrolylpolyenes in Auxarthron umbrinum.
abstract: The biosynthesis of the pyrrolylpolyene rumbrin (1) in the fungus Auxarthron umbrinum was elucidated using feeding studies with labelled precursors. Incorporation of stable isotopes from [(15)N]-proline, [(13)C]-methionine and [(13)C]-acetate confirmed that these were the precursors of the pyrrole moiety, methyl groups, and backbone of rumbrin, respectively. Label-dilution experiments with pyrrole-2-carboxylate confirmed it was a direct precursor in the biosynthesis of rumbrin. Both 3- and 4-chloropyrrolecarboxylates were also accepted as precursors in polyene production.
authors.affiliation: School of Biomolecular and Biomedical Sciences, Centre for Synthesis and Chemical Biology, Ardmore House, University College Dublin, Belfield, Dublin 4, Republic of Ireland.
authors.forename: Benjamin R
authors.initials: BR
authors.lastname: Clark
authors.forename: Cormac D
authors.initials: CD
authors.lastname: Murphy
mesh_terms: D002264:Carboxylic Acids / Q000737:chemistry; D002626:Chemistry, Pharmaceutical / Q000379:methods; D002713:Chlorine / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D004305:Dose-Response Relationship, Drug; D015195:Drug Design; D005658:Fungi / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D008715:Methionine / Q000737:chemistry; D008956:Models, Chemical; D011090:Polyenes / Q000737:chemistry; D011758:Pyrroles / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet / Q000379:methods; D013997:Time Factors
chemical_list: D002264:Carboxylic Acids; D011090:Polyenes; D011758:Pyrroles; D002713:Chlorine; D008715:Methionine