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Science Highlight July 2005 Structural Basis for the Promiscuous Biosynthetic Prenylation of Aromatic Natural Products Tomohisa Kuzuyama1 2 Joseph P Noel1 St phane B Richard1 1 Jack Skirball Chemical Biology and Proteomics Laboratory The Salk Institute for Biological Studies 10010 North Torrey Pines Road La Jolla California 92037 USA 2 Laboratory of Cell Biotechnology Biotechnology Research Center The University of Tokyo 1 1 1 Yayoi Bunkyo ku Tokyo 113 8657 Japan Prenylation is a general term for the chemical or enzymatic addition of a hydrophobic isoprenoid side chain to an accepting molecule another isoprenoid chemical small aromatic molecule protein etc Prenylation of aromatic natural products plays a critical role in the biosynthesis of chemically complex and structurally diverse molecules playing important biological functions across a wide phylogenetically diverse group of organisms from bacteria to mammals Hybrid natural products such 1 3 that contain a polyketide core decorated with 5as the anti oxidant naphterpin carbon dimethylallyl 10 carbon geranyl or 15 carbon farnesyl isoprenoid chains possess biological activities distinct from their non prenylated aromatic precursors4 These hybrid natural products represent new anti microbial anti oxidant antiinflammatory anti viral and anti cancer compounds Enzymes capable of regiospecific prenylation of bioactive compounds will serve as novel chemoenzymatic tools for natural product diversification and the chemoenzymatic development of therapeutically novel synthetic compounds We recently reported the gene identification biochemical characterization and high resolution crystal structure of an architecturally novel aromatic prenyltransferase PTase Orf2 from Streptomyces sp strain CL190 This protein belongs to a recently identified and completely new class of aromatic prenyltransferases showing no sequence similarity with any protein prenyltransferase5 The three dimensional structure of Orf2 consists of a single



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