Heterologous biosynthesis of amidated polyketides with novel cyclization regioselectivity from oxytetracycline polyketide synthase

被引：17

作者：

Zhang, Wenjun

Watanabe, Kenji

Wang, Clay C. C.

Tang, Yi ^{[1
]}

机构：

[1] Univ Calif Los Angeles, Dept Chem & Biomol Engn, Los Angeles, CA USA

[2] Univ So Calif, Sch Pharm, Dept Pharmaceut Sci, Los Angeles, CA 90033 USA

来源：

JOURNAL OF NATURAL PRODUCTS | 2006年 / 69卷 / 11期

关键词：

D O I：

10.1021/np060290i

中图分类号：

Q94 [植物学];

学科分类号：

071001 ;

摘要：

Heterologous expression of the minimal oxytetracycline polyketide synthase and the amidotransferase OxyD in Streptomyces coelicolor strain CH999 afforded two novel amidated polyketides, WJ85 (4) and WJ85b (5). WJ85 is a C-9 unreduced decaketide that is primed by a malonamyl starter unit. WJ85 is cyclized via an unusual C-11 to C-16 intramolecular aldol condensation not observed among known aromatic polyketides. The structures of WJ85 and the previously characterized WJ35 suggest that the presence of an amide starter unit has a profound effect on the cyclization regioselectivity and reactivity of a polyketide backbone. WJ85b is an anthraquinone and is an oxidized product of WJ85.

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页码：1633 / 1636

页数：4

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