Divergent biosynthesis of indole alkaloids FR900452 and spiro-maremycins†,Organic & Biomolecular Chemistry

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Divergent biosynthesis of indole alkaloids FR900452 and spiro-maremycins†
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2018-07-18 00:00:00 , DOI: 10.1039/c8ob01181h
Yingyi Duan _{1,

2,

3,

4,

5} , Yanyan Liu _{1,

2,

3,

4,

5} , Tao Huang _{6,

7,

8,

9} , Yi Zou _{9,

10,

11,

12} , Tingting Huang _{1,

2,

3,

4,

5} , Kaifeng Hu _{6,

7,

8,

9} , Zixin Deng _{1,

2,

3,

4,

5} , Shuangjun Lin _{1,

2,

3,

4,

5}

Affiliation

FR900452 and spirocyclic maremycins, including F and G components, are structurally related indole alkaloids, previously identified from different Streptomyces species. These alkaloids feature an indole diketopiperazine motif linked with a cyclopentenone moiety, but the linkage differs in FR900452 and the spirocyclic maremycins. Here, FR900452 and its two new analogues were identified from the fermentation broth of Streptomyces sp. B9173, the producer of maremycins. Gene inactivation and heterologous expression of the mar gene cluster confirmed that production of FR900452 shares the same biosynthetic machinery that produces maremycins. FR900452 was identified as the precursor of maremycin A/B by feeding studies. MarP, a SnoaL-like protein, was demonstrated to differentiate the biosynthesis of FR900452 from that of spiro-form maremycin G.

中文翻译：

吲哚生物碱FR900452和螺旋螺旋霉素的不同生物合成†

FR900452和螺环霉素，包括F和G成分，是与结构相关的吲哚生物碱，先前已从不同的链霉菌种中鉴定出来。这些生物碱具有与环戊烯酮部分连接的吲哚二酮哌嗪基序，但在FR900452和螺环马来霉素中的连接不同。在这里，从链霉菌属的发酵液中鉴定了FR900452及其两个新的类似物。B9173，maremycins的生产商。mar的基因失活和异源表达基因簇证实，FR900452的生产与产生mar霉素的生物合成机制相同。通过进食研究，FR900452被确定为马雷霉素A / B的前体。已证明MarP是一种SnoaL样蛋白，可将FR900452的生物合成与螺旋形式的变形霉素G区别开。

更新日期：2018-07-18

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