title: Assignment of the CD Cotton Effect to the Chiral Center in Pseurotins, and the Stereochemical Revision of Pseurotin A₂.
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.
authors.affiliation: Medicinal Chemistry Laboratory, Osaka University of Pharmaceutical Sciences, 4-20-1, Nasahara, Takatsuki, Osaka 569-1094, Japan. yamada@gly.oups.ac.jp.
authors.forename: Takeshi
authors.initials: T
authors.lastname: Yamada
authors.affiliation: Medicinal Chemistry Laboratory, Osaka University of Pharmaceutical Sciences, 4-20-1, Nasahara, Takatsuki, Osaka 569-1094, Japan. skr-dh.mc-tp.128@ezweb.ne.jp.
authors.forename: Mina
authors.initials: M
authors.lastname: Ohshima
authors.affiliation: Medicinal Chemistry Laboratory, Osaka University of Pharmaceutical Sciences, 4-20-1, Nasahara, Takatsuki, Osaka 569-1094, Japan. k.m.k.l.v.k@gmail.com.
authors.forename: Kaori
authors.initials: K
authors.lastname: Yuasa
authors.affiliation: Medicinal Chemistry Laboratory, Osaka University of Pharmaceutical Sciences, 4-20-1, Nasahara, Takatsuki, Osaka 569-1094, Japan. t.kikuchi@gly.oups.ac.jp.
authors.forename: Takashi
authors.initials: T
authors.lastname: Kikuchi
authors.affiliation: Medicinal Chemistry Laboratory, Osaka University of Pharmaceutical Sciences, 4-20-1, Nasahara, Takatsuki, Osaka 569-1094, Japan. tanakar@gly.oups.ac.jp.
authors.forename: Reiko
authors.initials: R
authors.lastname: Tanaka
mesh_terms: D000818:Animals; D001232:Aspergillus fumigatus / Q000378:metabolism; D005399:Fishes / Q000382:microbiology; D015394:Molecular Structure; D011760:Pyrrolidinones / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D011760:Pyrrolidinones; C012013:pseurotin
keywords: Aspergillus fumigatus; cephalimysins; marine fish; marine microorganism; pseurotins; spiro-heterocyclic γ-lactam