Roseopurpurins: Chemical Diversity Enhanced by Convergent Biosynthesis and Forward and Reverse Michael Additions

Zhuo Shang; Zeinab Khalil; Li Li; Angela A. Salim; Michelle Quezada; Pabasara Kalansuriya; Robert J. Capon

doi:10.1021/acs.orglett.6b02099

Roseopurpurins: Chemical Diversity Enhanced by Convergent Biosynthesis and Forward and Reverse Michael Additions

Zhuo Shang, Zeinab Khalil, Li Li, Angela A. Salim, Michelle Quezada, Pabasara Kalansuriya, Robert J. Capon

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

20 Citations (Scopus)

Abstract

Cultures of the estuarine fungus Penicillium roseopurpureum (CMB-MF038) yielded a diverse array of polyketides, many of which were related via a highly convergent biosynthetic pathway. In addition to revising and assigning structures, and documenting chemical and biological properties, pro-drug cytotoxic properties were attributed to roseopurpurins H (10) and I (11) on the basis of in situ reverse Michael addition to a cytotoxic Michael acceptor (12).

Original language	English
Pages (from-to)	4340-4343
Number of pages	4
Journal	Organic Letters
Volume	18
Issue number	17
DOIs	https://doi.org/10.1021/acs.orglett.6b02099
Publication status	Published - 2 Sept 2016
Externally published	Yes

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abstract = "Cultures of the estuarine fungus Penicillium roseopurpureum (CMB-MF038) yielded a diverse array of polyketides, many of which were related via a highly convergent biosynthetic pathway. In addition to revising and assigning structures, and documenting chemical and biological properties, pro-drug cytotoxic properties were attributed to roseopurpurins H (10) and I (11) on the basis of in situ reverse Michael addition to a cytotoxic Michael acceptor (12).",

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AU - Shang, Zhuo

AU - Khalil, Zeinab

AU - Li, Li

AU - Salim, Angela A.

AU - Quezada, Michelle

AU - Kalansuriya, Pabasara

AU - Capon, Robert J.

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AB - Cultures of the estuarine fungus Penicillium roseopurpureum (CMB-MF038) yielded a diverse array of polyketides, many of which were related via a highly convergent biosynthetic pathway. In addition to revising and assigning structures, and documenting chemical and biological properties, pro-drug cytotoxic properties were attributed to roseopurpurins H (10) and I (11) on the basis of in situ reverse Michael addition to a cytotoxic Michael acceptor (12).

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Roseopurpurins: Chemical Diversity Enhanced by Convergent Biosynthesis and Forward and Reverse Michael Additions

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