Assignment of Absolute Configuration of Bromoallenes by Vacuum-Ultraviolet Circular Dichroism (VUVCD)

Umezawa, Taiki; Mizutani, Nakaba; Matsuo, Koichi; Tokunaga, Yuugo; Matsuda, Fuyuhiko; Nehira, Tatsuo

Assignment of Absolute Configuration of Bromoallenes by Vacuum-Ultraviolet Circular Dichroism (VUVCD)

Umezawa, Taiki; Mizutani, Nakaba; Matsuo, Koichi et al.

Molecules, 2021, 26(5), 1296

Permalink : https://hdl.handle.net/2115/81343

このアイテムのアクセス数:662件（2026-08-15 22:54 集計）

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論文情報

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アクセス権	open access
URI	https://hdl.handle.net/2115/81343
タイトル	Assignment of Absolute Configuration of Bromoallenes by Vacuum-Ultraviolet Circular Dichroism (VUVCD)
著者	Umezawa, Taiki ; Mizutani, Nakaba ; Matsuo, Koichi ; Tokunaga, Yuugo ; Matsuda, Fuyuhiko ; Nehira, Tatsuo
e-Rad_Researcher 20503618 著者名 Umezawa, Taiki
著者名 Mizutani, Nakaba
e-Rad_Researcher 40403620 著者名 Matsuo, Koichi
著者名 Tokunaga, Yuugo
e-Rad_Researcher 10219446 著者名 Matsuda, Fuyuhiko
e-Rad_Researcher 60321692 著者名 Nehira, Tatsuo
言語	英語
キーワード	bromoallene
	structure determination
	VUVCD
	Lowe’s rule
	natural product
発行日	2021-03-01
出版者	MDPI
収録物名	Molecules
巻(号)	26(5)
ページ	1296
抄録	A new application of vacuum-ultraviolet circular dichroism (VUVCD), which enables the measurement of CD spectra in the vacuum-ultraviolet region (140-200 nm), for the assignment of the absolute configurations of bromoallenes is described. Bromoallene moieties are found in natural products obtained from many marine organisms. To date, the absolute configuration of bromoallenes has been assigned almost exclusively with Lowe's rule, which is based on specific rotation. However, exceptions to Lowe's rule have been reported arising from the presence of other substituents with large specific rotations. For the unambiguous assignment of the absolute configuration of the bromoallene moiety with its characteristic absorption wavelength at 180-190 nm due to the pi-pi* transition, VUVCD was applied to four pairs of bromoallene diastereomers prepared by modifying the synthetic scheme of omaezallene. The VUVCD spectra clearly showed positive or negative Cotton effects around 180-190 nm according to the configuration of the bromoallene employed, revealing the potential of VUVCD for determining absolute stereochemistry.
資源タイプ	学術雑誌論文
出版タイプ	Version of Record
権利情報	Creative Commons Attribution 4.0 International
PISSN	1420-3049
関連情報 (isIdenticalTo)	出版社版DOI https://doi.org/10.3390/molecules26051296