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Non-Heme Iron Enzymes Catalyze Heterobicyclic and Spirocyclic Isoquinolone Core Formation in Piperazine Alkaloid Biosynthesis.
Pham, Mai-Truc; Yang, Feng-Ling; Liu, I-Chen; Liang, Po-Huang; Lin, Hsiao-Ching.
Afiliação
  • Pham MT; Institute of Biological Chemistry, Academia Sinica, Taipei, 115, Taiwan R.O.C.
  • Yang FL; Chemical Biology and Molecular Biophysics Program, Taiwan International Graduate Program, Academia Sinica, Taipei, 115, Taiwan R.O.C.
  • Liu IC; Department of Chemistry, National Tsing Hua University, Hsinchu, 300, Taiwan R.O.C.
  • Liang PH; Institute of Biological Chemistry, Academia Sinica, Taipei, 115, Taiwan R.O.C.
  • Lin HC; Chemical Biology and Molecular Biophysics Program, Taiwan International Graduate Program, Academia Sinica, Taipei, 115, Taiwan R.O.C.
Angew Chem Int Ed Engl ; 63(20): e202401324, 2024 05 13.
Article em En | MEDLINE | ID: mdl-38499463
ABSTRACT
We report the discovery and biosynthesis of new piperazine alkaloids-arizonamides, and their derived compounds-arizolidines, featuring heterobicyclic and spirocyclic isoquinolone skeletons, respectively. Their biosynthetic pathway involves two crucial non-heme iron enzymes, ParF and ParG, for core skeleton construction. ParF has a dual function facilitating 2,3-alkene formation of helvamide, as a substrate for ParG, and oxidative cleavage of piperazine. Notably, ParG exhibits catalytic versatility in multiple oxidative reactions, including cyclization and ring reconstruction. A key amino acid residue Phe67 was characterized to control the formation of the constrained arizonamide B backbone by ParG.
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Alcaloides Idioma: En Revista: Angew Chem Int Ed Engl Ano de publicação: 2024 Tipo de documento: Article

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Alcaloides Idioma: En Revista: Angew Chem Int Ed Engl Ano de publicação: 2024 Tipo de documento: Article