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

James D. Sunderhaus; Timothy J. McAfoos; Jennifer M. Finefield; Hikaru Kato; Shengying Li; Sachiko Tsukamoto; David H. Sherman; Robert M. Williams

doi:10.1021/ol302901p

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

James D. Sunderhaus, Timothy J. McAfoos, Jennifer M. Finefield, Hikaru Kato, Shengying Li, Sachiko Tsukamoto, David H. Sherman, Robert M. Williams

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32 Scopus citations

Abstract

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 is 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.

Original language	English (US)
Pages (from-to)	22-25
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	1
DOIs	https://doi.org/10.1021/ol302901p
State	Published - Jan 4 2013
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol302901p

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title = "Synthesis and bioconversions of notoamide T: A biosynthetic precursor to stephacidin A and notoamide B",

abstract = "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 is 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.",

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T1 - Synthesis and bioconversions of notoamide T

T2 - A biosynthetic precursor to stephacidin A and notoamide B

AU - Sunderhaus, James D.

AU - McAfoos, Timothy J.

AU - Finefield, Jennifer M.

AU - Kato, Hikaru

AU - Li, Shengying

AU - Tsukamoto, Sachiko

AU - Sherman, David H.

AU - Williams, Robert M.

PY - 2013/1/4

Y1 - 2013/1/4

N2 - 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 is 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.

AB - 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 is 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.

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

Abstract

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