Synthesis and bioconversions of notoamide T: a biosynthetic precursor to stephacidin A and notoamide B.

Synthesis and bioconversions of notoamide T: a biosynthetic precursor to stephacidin A and notoamide B.
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DOI:
10.1021/ol302901p
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发表时间:
2013-01-04
期刊:
影响因子:
5.2
通讯作者:
Williams, Robert M.
Williams, Robert M.
中科院分区:
化学1区
文献类型:
--
作者:
Sunderhaus, James D.;McAfoos, Timothy J.;Finefield, Jennifer M.;Kato, Hikaru;Li, Shengying;Tsukamoto, Sachiko;Sherman, David H.;Williams, Robert M.

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为了进一步阐明千金藤素和notoamide家族天然产物的生物起源,notoamide T已被鉴定为千金藤素A的可能前体。沿着叙述了三七酰胺T及其C-6-差向异构体6-表三七酰胺T的全合成。描述了通过还原性开环将千金藤素A化学转化为notoamide T,以及将notoamide T氧化转化为千金藤素A。此外,还合成了[13 C]2-三七酰胺T,并将其提供给杂色曲霉和曲霉属MF 297 -2,在其高级代谢产物三七酰胺B中观察到显著掺入。
In an effort to further elucidate the biogenesis of the stephacidin and notoamide families of natural products, notoamide T has been identified as the likely precursor to stephacidin A. The total synthesis of notoamide T is described along with it's C-6-epimer, 6-epi-notoamide T. The chemical conversion of stephacidin A to notoamide T by reductive ring-opening is described as well as the oxidative conversion of notoamide T to stephacidin A. Furthermore, [13C]2-notoamide T was synthesized and provided to Aspergillus versicolor and Aspergillus sp. MF297-2, in which significant incorporation was observed in the advanced metabolite, notoamide B.
DOI: 10.1021/jo100332c
发表时间: 2010-05-07
影响因子: 3.6
作者:
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通讯作者: Williams, Robert M.
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发表时间: 2007-01-01
影响因子: 16.6
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