Rapid and Controllable Hydrogen/Deuterium Exchange on Aromatic Rings of α-Amino Acids and Peptides

Murai, Yuta; Wang, Lei; Masuda, Katsuyoshi; Sakihama, Yasuko; Hashidoko, Yasuyuki; Hatanaka, Yasumaru; Hashimoto, Makoto

Rapid and Controllable Hydrogen/Deuterium Exchange on Aromatic Rings of α-Amino Acids and Peptides

Murai, Yuta; Wang, Lei; Masuda, Katsuyoshi et al.

European Journal of Organic Chemistry, 2013, 2013(23), 5111-5116

Permalink : https://hdl.handle.net/2115/64885

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アクセス権	open access
URI	https://hdl.handle.net/2115/64885
タイトル	Rapid and Controllable Hydrogen/Deuterium Exchange on Aromatic Rings of α-Amino Acids and Peptides
著者	Murai, Yuta ; Wang, Lei ; Masuda, Katsuyoshi ; Sakihama, Yasuko ; Hashidoko, Yasuyuki ; Hatanaka, Yasumaru ; Hashimoto, Makoto
著者名 Murai, Yuta
著者名 Wang, Lei
著者名 Masuda, Katsuyoshi
e-Rad_Researcher 10344491 著者名 Sakihama, Yasuko
e-Rad_Researcher 40281795 著者名 Hashidoko, Yasuyuki
著者名 Hatanaka, Yasumaru
e-Rad_Researcher 90292094 著者名 Hashimoto, Makoto
言語	英語
キーワード	Hydrogen-deuterium exchange
	Aromatic α-amino acids
	Trifluoromethanesulfonic acid-D (TfOD)
	MSMS analysis
	Enzymatic digestion
発行日	2013-08
出版者	Wiley-VCH
収録物名	European Journal of Organic Chemistry
巻(号)	2013(23)
ページ	5111-5116
抄録	Novel hydrogen/deuterium exchange for aromatic α-amino acids and their corresponding peptides were performed through the use of deuterated trifluoromethanesulfonic acid (TfOD). Detailed analysis of the exchange revealed that equal hydrogen/deuterium exchange was observed for phenylalanine, and specific exchange at the ortho-positions of phenol for tyrosine was also detected. The stereochemistry of the aromatic α-amino acids was retained under the exchange conditions. The hydrogen/deuterium exchange properties for these aromatic α-amino acids are identical for peptides that contain several aromatic α-amino acids. The exchange proceeded significantly faster than previous methods. Detailed analysis of the exchange revealed that the method could be controlled by temperature, time, and the amount of reagent.
資源タイプ	学術雑誌論文
出版タイプ	Accepted Manuscript
権利情報	This is the peer reviewed version of the following article: Rapid and Controllable Hydrogen/Deuterium Exchange on Aromatic Rings of α-Amino Acids and Peptides, European Journal of Organic Chemistry, 2013(23), 5111-5116, which has been published in final form at 10.1002/ejoc.201300405. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.
PISSN	1434-193X
関連情報 (isVersionOf)	出版社版DOI https://doi.org/10.1002/ejoc.201300405