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Mar. Drugs 2016, 14(4), 74; doi:10.3390/md14040074

Assignment of the CD Cotton Effect to the Chiral Center in Pseurotins, and the Stereochemical Revision of Pseurotin A2

Medicinal Chemistry Laboratory, Osaka University of Pharmaceutical Sciences, 4-20-1, Nasahara, Takatsuki, Osaka 569-1094, Japan
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Academic Editor: Anake Kijjoa
Received: 3 February 2016 / Revised: 8 March 2016 / Accepted: 31 March 2016 / Published: 9 April 2016
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Abstract

Pseurotins A1 (1) and A2 (2) were ( S ) = [ (i,j ) ij ] i , j = 1 n isolated from a culture broth of the fungal strain Aspergillus fumigatus WFZ-25 as stereoisomers of pseurotin A (3) in 2011. We also isolated 1 and 2 together with 3 from A. fumigatus OUPS-T106B-5 separated from the marine fish Mugil cephalus. In this study, we re-examined the stereochemistry of 1 and 2 using chemical transformation and the CD spectra, and found the relationship between the CD Cotton effect and the absolute configurations of 1 and 2, which led us to revise the stereostructure of pseurotin A2. . View Full-Text
Keywords: pseurotins; Aspergillus fumigatus; marine microorganism; marine fish; cephalimysins; spiro-heterocyclic γ-lactam pseurotins; Aspergillus fumigatus; marine microorganism; marine fish; cephalimysins; spiro-heterocyclic γ-lactam
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MDPI and ACS Style

Yamada, T.; Ohshima, M.; Yuasa, K.; Kikuchi, T.; Tanaka, R. Assignment of the CD Cotton Effect to the Chiral Center in Pseurotins, and the Stereochemical Revision of Pseurotin A2. Mar. Drugs 2016, 14, 74.

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