title: Elucidating the cyclization cascades in xiamycin biosynthesis by substrate synthesis and enzyme characterizations.
abstract: Indolosesquiterpene xiamycin A features a pentacyclic core structure. The chemical synthesis of two key precursors, 3-farnesylindole and 3-(epoxyfarnesyl)-indole, allowed elucidation of the enzymatic cascades forming the pentacyclic ring system of xiamycin A by XiaO-catalyzed epoxidation and the membrane protein XiaH-catalyzed terpene cyclization. The substrate flexibility of XiaI, an indole oxygenase for assembly of the central ring, was also demonstrated.
authors.affiliation: Key Laboratory of Tropical Marine Bio-resources and Ecology, RNAM Center for Marine Microbiology, Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences , 164 West Xingang Road, Guangzhou 510301, China.
authors.forename: Huixian
authors.initials: H
authors.lastname: Li
authors.forename: Yu
authors.initials: Y
authors.lastname: Sun
authors.forename: Qingbo
authors.initials: Q
authors.lastname: Zhang
authors.forename: Yiguang
authors.initials: Y
authors.lastname: Zhu
authors.forename: Shu-Ming
authors.initials: SM
authors.lastname: Li
authors.forename: Ang
authors.initials: A
authors.lastname: Li
authors.forename: Changsheng
authors.initials: C
authors.lastname: Zhang
mesh_terms: D055162:Biocatalysis; D003500:Cyclization; D004792:Enzyme Precursors / Q000138:chemical synthesis* / Q000737:chemistry; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry*; D008565:Membrane Proteins / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010088:Oxidoreductases / Q000737:chemistry*; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D013729:Terpenes / Q000737:chemistry*
chemical_list: C000600332:3-(epoxyfarnesyl)-indole; C000600331:3-farnesylindole; D004792:Enzyme Precursors; D004852:Epoxy Compounds; D007211:Indoles; D008565:Membrane Proteins; D012717:Sesquiterpenes; D013729:Terpenes; C556785:xiamycin; C030374:indole; D010088:Oxidoreductases