Ansalactams B-D Illustrate Further Biosynthetic Plasticity within the Ansamycin Pathway

Tu Cam Le; Inho Yang; Yeo Joon Yoon; Sang Jip Nam; William Fenical

doi:10.1021/acs.orglett.6b00892

Ansalactams B-D Illustrate Further Biosynthetic Plasticity within the Ansamycin Pathway

Tu Cam Le, Inho Yang, Yeo Joon Yoon, Sang Jip Nam, William Fenical

Chemistry & Nanoscience

Research output: Contribution to journal › Article › peer-review

26 Scopus citations

Abstract

Further chemical investigation of a marine-derived bacterium of the genus Streptomyces has led to the isolation of ansalactams B-D (1-3) along with the previously reported metabolite ansalactam A (4). Ansalactams B-D are significantly modified ansamycins, representing three new carbon skeletons and further illustrating the biosynthetic plasticity of the ansalactam class. Unlike ansalactam A, ansalactams B and D are penta- and hexacyclic metabolites, while ansalactam C illustrates an open polyene chain with a terminal carboxylic acid.

Original language	English
Pages (from-to)	2256-2259
Number of pages	4
Journal	Organic Letters
Volume	18
Issue number	9
DOIs	https://doi.org/10.1021/acs.orglett.6b00892
State	Published - 6 May 2016

Bibliographical note

Funding Information:
The present study was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF), funded by the Ministry of Science, ICT and Future Planning (NRF- 2014R1A1A1003492 and NRF- 2016R1A2A1A05005078), and by the U.S. National Cancer Institute (NIH) under Grant No. R37CA044848 and Instrument Grant No. 1 S10 OD0106400-01A1 (HR?LC?MS, both to W.F.).

Publisher Copyright:
© 2016 American Chemical Society.

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title = "Ansalactams B-D Illustrate Further Biosynthetic Plasticity within the Ansamycin Pathway",

abstract = "Further chemical investigation of a marine-derived bacterium of the genus Streptomyces has led to the isolation of ansalactams B-D (1-3) along with the previously reported metabolite ansalactam A (4). Ansalactams B-D are significantly modified ansamycins, representing three new carbon skeletons and further illustrating the biosynthetic plasticity of the ansalactam class. Unlike ansalactam A, ansalactams B and D are penta- and hexacyclic metabolites, while ansalactam C illustrates an open polyene chain with a terminal carboxylic acid.",

author = "Le, {Tu Cam} and Inho Yang and Yoon, {Yeo Joon} and Nam, {Sang Jip} and William Fenical",

note = "Funding Information: The present study was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF), funded by the Ministry of Science, ICT and Future Planning (NRF- 2014R1A1A1003492 and NRF- 2016R1A2A1A05005078), and by the U.S. National Cancer Institute (NIH) under Grant No. R37CA044848 and Instrument Grant No. 1 S10 OD0106400-01A1 (HR?LC?MS, both to W.F.). Publisher Copyright: {\textcopyright} 2016 American Chemical Society.",

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AU - Le, Tu Cam

AU - Yang, Inho

AU - Yoon, Yeo Joon

AU - Nam, Sang Jip

AU - Fenical, William

N1 - Funding Information: The present study was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF), funded by the Ministry of Science, ICT and Future Planning (NRF- 2014R1A1A1003492 and NRF- 2016R1A2A1A05005078), and by the U.S. National Cancer Institute (NIH) under Grant No. R37CA044848 and Instrument Grant No. 1 S10 OD0106400-01A1 (HR?LC?MS, both to W.F.). Publisher Copyright: © 2016 American Chemical Society.

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AB - Further chemical investigation of a marine-derived bacterium of the genus Streptomyces has led to the isolation of ansalactams B-D (1-3) along with the previously reported metabolite ansalactam A (4). Ansalactams B-D are significantly modified ansamycins, representing three new carbon skeletons and further illustrating the biosynthetic plasticity of the ansalactam class. Unlike ansalactam A, ansalactams B and D are penta- and hexacyclic metabolites, while ansalactam C illustrates an open polyene chain with a terminal carboxylic acid.

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ER -

Ansalactams B-D Illustrate Further Biosynthetic Plasticity within the Ansamycin Pathway

Abstract

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