Hydrogen/deuterium exchange of cross-linkable α-amino acid derivatives in deuterated triflic acid. Issue 7 (3rd July 2014)

• Record Type: Journal Article
• Authors: Wang, Lei; Murai, Yuta; Yoshida, Takuma; Okamoto, Masashi; Masuda, Katsuyoshi; Sakihama, Yasuko; Hashidoko, Yasuyuki; Hatanaka, Yasumaru; Hashimoto, Makoto
• Is Part Of: Bioscience, biotechnology, and biochemistry. Volume 78:Issue 7(2014)
• Page Start: 1129
• Page End: 1134
• Publication Date: 2014-07-03
• Subjects: Hydrogen/deuterium exchange -- aromatic α-amino acid -- cross-link -- photophore -- triflic acid; Biotechnology -- Periodicals; Biochemistry -- Periodicals; 660.6
• DOI: 10.1080/09168451.2014.917267
• Languages: English
• ISSNs: 0916-8451

Abstract

Abstract: In this paper we report here a hydrogen/deuterium exchange (H/D exchange) of cross-linkable α-amino acid derivatives with deuterated trifluoromethanesulfonic acid (TfOD). H/D exchange with TfOD was easily applied to o -catechol containing phenylalanine (DOPA) within an hour. A partial H/D exchange was observed for trifluoromethyldiazirinyl (TFMD) phenylalanine derivatives. N -Acetyl-protected natural aromatic α-amino acids (Tyr and Trp) were more effective in H/D exchange than unprotected ones. The N -acetylated TFMD phenylalanine derivative afforded slightly higher H/D exchange than unprotected derivatives. An effective post-deuteration method for cross-linkable α-amino acid derivatives will be useful for the analysis of biological functions of bioactive peptides and proteins by mass spectrometry. Graphical abstract: : Hydrogen-deuterium exchange of cross-linkable α-amino acid derivatives in deuterated triflic acid proceeded smoothly at low temperature.