Assignment of the CD Cotton Effect to the Chiral Center in Pseurotins,and the Stereochemical Revision of Pseurotin A2 |
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| Authors: | Takeshi Yamada Mina Ohshima Kaori Yuasa Takashi Kikuchi Reiko Tanaka |
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| Affiliation: | Medicinal Chemistry Laboratory, Osaka University of Pharmaceutical Sciences, 4-20-1, Nasahara, Takatsuki, Osaka 569-1094, Japan; (M.O.); (K.Y.); (T.K.); (R.T.) |
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| Abstract: | Pseurotins A1 (1) and A2 (2) were 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. |
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| Keywords: | pseurotins, Aspergillus fumigatus, marine microorganism, marine fish, cephalimysins, spiro-heterocyclic γ -lactam |
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