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

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Please use this identifier to cite or link to this item:http://hdl.handle.net/2115/64885

Title: Rapid and Controllable Hydrogen/Deuterium Exchange on Aromatic Rings of α-Amino Acids and Peptides
Authors: Murai, Yuta Browse this author
Wang, Lei Browse this author
Masuda, Katsuyoshi Browse this author
Sakihama, Yasuko Browse this author →KAKEN DB
Hashidoko, Yasuyuki Browse this author →KAKEN DB
Hatanaka, Yasumaru Browse this author
Hashimoto, Makoto Browse this author →KAKEN DB
Keywords: Hydrogen-deuterium exchange
Aromatic α-amino acids
Trifluoromethanesulfonic acid-D (TfOD)
MSMS analysis
Enzymatic digestion
Issue Date: Aug-2013
Publisher: Wiley-VCH
Journal Title: European Journal of Organic Chemistry
Volume: 2013
Issue: 23
Start Page: 5111
End Page: 5116
Publisher DOI: 10.1002/ejoc.201300405
Abstract: 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.
Rights: 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.
Type: article (author version)
URI: http://hdl.handle.net/2115/64885
Appears in Collections:農学院・農学研究院 (Graduate School of Agriculture / Faculty of Agriculture) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 橋本 誠

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