Gene-Inspired Mycosynthesis of Skeletally New Indole Alkaloids
Gene-Inspired Mycosynthesis of Skeletally New Indole Alkaloids
复制标题
骨骼新吲哚生物碱的基因启发真菌合成
DOI：
10.1021/acs.orglett.5b00882
复制
发表时间：
2015-06-05
期刊：
影响因子：
5.2
通讯作者：
Tan, Ren Xiang
中科院分区：
文献类型：
--
作者：
Lin, Li Ping;Yuan, Peng;Tan, Ren Xiang
Dalesindole是一种具有未知碳骨架的吲哚类生物碱，是由黑煤轮状炭壳菌（Daldinia eschscholzii）在单加氧酶和8-氨基-7-氧代壬酸合酶（AONS）的催化下，通过真菌色酮与吲哚-3-甲醇（I3 C）原位生成的3，3 '-二吲哚基甲烷（DIM）的II类醛缩酶催化Michael加成反应，立体选择性地合成的。达来吲哚通过逆迈克尔反应异构化，得到具有生物活性的立体异构体。这项工作提供了一个新的生物活性杂交真菌寡酮与微生物修饰的外源化学。
Dalesindole, an antibacterial and anti-inflammatory indole alkaloid with an undescribed carbon skeleton, was stereoselectively constructed by Daldinia eschscholzii through class II aldolase catalyzed Michael addition of fungal chromone with 3,3'-diindolylmethane (DIM) formed in situ from indole-3-carbinol (I3C) under catalyses of monooxygenase and 8-amino-7-oxononanoate synthase (AONS). Dalesindole isomerizes via a retro-Michael reaction to give stereoisomers with bioactivities. The work provides an access to new bioactive hybrids of fungal oligoketide with microbially decorated exogenous chemistry.