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An enzymatic [4+2] cyclization cascade creates the pentacyclic core of pyrroindomycins
Alternative Title酶催化[4+2]环加成串联反应创建吡咯吲哚酸的五环核心
Tian ZH(田振华)1; Sun P(孙鹏)1; Yan Y(闫岩)1; Wu ZH(吴竹华)1; Zheng QF(郑庆飞)1; Zhou SX(周帅祥)1; Zhang H(张华)1; Yu FT(于福涛)1; Jia XY(贾新颖)1; Chen DD(陈单丹)1; MANDI ATTILA1; KURTAN TIBOR1; Liu W(刘文)1
Source PublicationNat. Chem. Biol.
AbstractThe [4+2] cycloaddition remains one of the most intriguing transformations in synthetic and natural products chemistry. In nature, however, there are remarkably few enzymes known to have this activity. We herein report an unprecedented enzymatic [4+2] cyclization cascade that has a central role in the biosynthesis of pyrroindomycins, which are pentacyclic spirotetramate natural products. Beginning with a linear intermediate that contains two pairs of 1,3-diene and alkene groups, the dedicated cyclases PyrE3 and PyrI4 act in tandem to catalyze the formation of two cyclohexene rings in the dialkyldecalin system and the tetramate spiro-conjugate of the molecules. The two cyclizations are completely enzyme dependent and proceed in a regio- and stereoselective manner to establish the enantiomerically pure pentacyclic core. Analysis of a related spirotetronate pathway confirms that homologs are functionally exchangeable, establishing the generality of these findings and explaining how nature creates diverse active molecules with similar rigid scaffolds.
Subject Area生命有机化学
Indexed BySCI
WOS IDWOS:000351666500007
Citation statistics
Cited Times:64[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Corresponding AuthorLiu W(刘文)
Affiliation1.中科院上海有机化学研究所, 生命有机化学国家重点实验室
Recommended Citation
GB/T 7714
Tian ZH,Sun P,Yan Y,et al. An enzymatic [4+2] cyclization cascade creates the pentacyclic core of pyrroindomycins[J]. Nat. Chem. Biol.,2015,11(4):259-265.
APA 田振华.,孙鹏.,闫岩.,吴竹华.,郑庆飞.,...&刘文.(2015).An enzymatic [4+2] cyclization cascade creates the pentacyclic core of pyrroindomycins.Nat. Chem. Biol.,11(4),259-265.
MLA 田振华,et al."An enzymatic [4+2] cyclization cascade creates the pentacyclic core of pyrroindomycins".Nat. Chem. Biol. 11.4(2015):259-265.
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