2024-03-28T22:37:56Zhttps://eprints.lib.hokudai.ac.jp/dspace-oai/requestoai:eprints.lib.hokudai.ac.jp:2115/648852022-11-17T02:08:08Zhdl_2115_20046hdl_2115_138Rapid and Controllable Hydrogen/Deuterium Exchange on Aromatic Rings of α-Amino Acids and PeptidesMurai, YutaWang, LeiMasuda, Katsuyoshi1000010344491Sakihama, Yasuko1000040281795Hashidoko, YasuyukiHatanaka, Yasumaru1000090292094Hashimoto, Makotoopen accessThis 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.Hydrogen-deuterium exchangeAromatic α-amino acidsTrifluoromethanesulfonic acid-D (TfOD)MSMS analysisEnzymatic digestionNovel 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.Wiley-VCH2013-08engjournal articleAMhttp://hdl.handle.net/2115/64885https://doi.org/10.1002/ejoc.2013004051434-193XEuropean Journal of Organic Chemistry20132351115116https://eprints.lib.hokudai.ac.jp/dspace/bitstream/2115/64885/3/11%20EJOC%2023%205111-5116.pdfapplication/pdf381.22 KB2013-08