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.
引用
收藏
页码：1633 / 1636
页数：4
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