Total Synthesis and Stereochemical Assignment of Burkholdac B, a Depsipeptide HDAC Inhibitor

Hanae Benelkebir; Alison M. Donlevy; Graham Packham; A. Ganesan

doi:10.1021/ol202197q

Total Synthesis and Stereochemical Assignment of Burkholdac B, a Depsipeptide HDAC Inhibitor

Hanae Benelkebir, Alison M. Donlevy, Graham Packham, A. Ganesan

School of Pharmacy

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

34 Citations (Scopus)

Abstract

Three diastereomers of burkholdac B were prepared by total synthesis, enabling the full stereochemical assignment of the natural product. It is proposed that burkholdac B is identical to thailandepsin A independently isolated by Cheng from the same strain of Burkholderia thailandensis. Burkholdac B is the most potent among depsipeptide histone deacetylase inhibitors in growth inhibition of the MCF7 breast cancer cell line with an IC50 of 60 pM. © 2011 American Chemical Society.

Original language	English
Pages (from-to)	6334-6337
Number of pages	4
Journal	Organic Letters
Volume	13
Issue number	24
DOIs	https://doi.org/10.1021/ol202197q
Publication status	Published - 2011

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10.1021/ol202197q

Cite this

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title = "Total Synthesis and Stereochemical Assignment of Burkholdac B, a Depsipeptide HDAC Inhibitor",

abstract = "Three diastereomers of burkholdac B were prepared by total synthesis, enabling the full stereochemical assignment of the natural product. It is proposed that burkholdac B is identical to thailandepsin A independently isolated by Cheng from the same strain of Burkholderia thailandensis. Burkholdac B is the most potent among depsipeptide histone deacetylase inhibitors in growth inhibition of the MCF7 breast cancer cell line with an IC50 of 60 pM. {\textcopyright} 2011 American Chemical Society.",

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AU - Donlevy, Alison M.

AU - Packham, Graham

AU - Ganesan, A.

PY - 2011

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AB - Three diastereomers of burkholdac B were prepared by total synthesis, enabling the full stereochemical assignment of the natural product. It is proposed that burkholdac B is identical to thailandepsin A independently isolated by Cheng from the same strain of Burkholderia thailandensis. Burkholdac B is the most potent among depsipeptide histone deacetylase inhibitors in growth inhibition of the MCF7 breast cancer cell line with an IC50 of 60 pM. © 2011 American Chemical Society.

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JF - Organic Letters

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