title: Direct biosynthetic cyclization of a distorted paracyclophane highlighted by double isotopic labelling of L-tyrosine.
abstract: The biosynthesis of pyrrocidines, fungal PK-NRP compounds featuring a strained [9]paracyclophane, was investigated in Acremonium zeae. We used a synthetic L-tyrosine probe, labelled with oxygen 18 as a reporter of phenol reactivity and carbon 13 as a tracer of incorporation of this exogenous precursor. The ((18)O)phenolic oxygen was incorporated, suggesting that phenol behaves as a nucleophile during the formation of the bent aryl ether.
authors: Muséum National d'Histoire Naturelle and Centre National de la Recherche Scientifique (joint unit UMR 7245 CNRS-MNHN), 57 rue Cuvier (CP 54), 75005 Paris, France. buisson@mnhn.fr bnay@mnhn.fr.
authors: Alexandre
authors: A
authors: Ear
authors: Séverine
authors: S
authors: Amand
authors: Florent
authors: F
authors: Blanchard
authors: Alain
authors: A
authors: Blond
authors: Lionel
authors: L
authors: Dubost
authors: Didier
authors: D
authors: Buisson
authors: Bastien
authors: B
authors: Nay
mesh_terms: D000164:Acremonium / Q000378:metabolism; D053898:Biosynthetic Pathways; D002851:Chromatography, High Pressure Liquid; D018360:Crystallography, X-Ray; D003500:Cyclization; D006576:Heterocyclic Compounds, 4 or More Rings / Q000737:chemistry; D007553:Isotope Labeling; D013058:Mass Spectrometry; D010880:Piperidines / Q000737:chemistry*; D011083:Polycyclic Compounds / Q000737:chemistry*; D011760:Pyrrolidinones / Q000737:chemistry; D013237:Stereoisomerism; D014443:Tyrosine / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism*
chemical_list: C479319:GKK1032A-2; D006576:Heterocyclic Compounds, 4 or More Rings; D010880:Piperidines; D011083:Polycyclic Compounds; D011760:Pyrrolidinones; D014443:Tyrosine