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Org Lett. 2020 Feb 21;22(4):1275-1279. doi: 10.1021/acs.orglett.9b04535. Epub 2020 Feb 4.

MS-Derived Isotopic Fine Structure Reveals Forazoline A as a Thioketone-Containing Marine-Derived Natural Product.

Author information

1
Pharmaceutical Sciences Division , University of Wisconsin-Madison , Madison , Wisconsin 53705 , United States.
2
Merck & Co., Inc. , 320 Bent Street , Cambridge , Massachusetts 02141 , United States.
3
Department of Cell and Regenerative Biology , University of Wisconsin-Madison , Madison , Wisconsin 53706 , United States.
4
Human Proteomics Program, School of Medicine and Public Health , University of Wisconsin-Madison , Madison , Wisconsin 53706 , United States.
5
Department of Chemistry , University of Wisconsin-Madison , Madison , Wisconsin 53706 , United States.
6
Department of Genetics , University of Wisconsin-Madison , Madison , Wisconsin 53706 , United States.
7
Department of Bacteriology , University of Wisconsin-Madison , Madison , Wisconsin 53706 , United States.

Abstract

Forazoline A is a structurally complex PKS-NRPS hybrid produced by marine-derived Actinomadura sp. During the course of studies highlighting the application of IFS analysis as a powerful tool for natural products analysis, we were alerted to an earlier misinterpretation with respect to forazoline A structure elucidation. In particular, IFS reveals that forazoline A contains a thioketone moiety rarely seen in secondary metabolites and, thus, constitutes an even more intriguing structure than originally thought.

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