Coronavirus Information for the UC San Diego Community

Our leaders are working closely with federal and state officials to ensure your ongoing safety at the university. Stay up to date with the latest developments. Learn more.

Asymmetric Alkene and Arene Halofunctionalization Reactions in Meroterpenoid Biosynthesis

TitleAsymmetric Alkene and Arene Halofunctionalization Reactions in Meroterpenoid Biosynthesis
Publication TypeJournal Article
Year of Publication2018
AuthorsMoore BS
Date Published2018/03
Type of ArticleArticle
ISBN Number0936-5214
Accession NumberWOS:000425173600010
Keywordsactinomycete; alpha-hydroxyketone rearrangement; biomimetic; biomimetic synthesis; chemistry; expression; gene-cluster; haloperoxidase; heterologous; identification; marine; meroterpenoid; napyradiomycins; Natural product biosynthesis; natural-products; polyketide synthase; Streptomyces; structural elucidation

Meroterpenoid natural products are important bioactive molecules with broad distribution throughout nature. In Streptomyces bacteria, naphthoquinone-based meroterpenoids comprise a simple yet structurally fascinating group of natural product antibiotics that are enzymatically constructed through a series of asymmetric alkene and arene halofunctionalization reactions. This account article highlights our discovery and characterization of a group of vanadium-dependent chloroperoxidase enzymes that catalyze halogen-assisted cyclization and rearrangement reactions and have inspired biomimetic syntheses of numerous meroterpenoid natural products. 1 Introduction 2 Early Biosynthetic Insights and the Characterization of Alkene Halofunctionalization in Napyradiomycin Biosynthesis 3 Discovery of the Merochlorin Natural Products and Enzymatic Aryl Halofunctionalization 4 Discovery and Development of Unifying THN-Based Meroterpenoid Biosynthesis and Synthesis Approaches 5 Insights into Naphterpin and Marinone Biosynthesis Involving Cryptic Aryl Halofunctionalization Reactions 6 Closing Thoughts

Student Publication: 
Research Topics: