title: Hydrogen/deuterium exchange of cross-linkable α-amino acid derivatives in deuterated triflic acid.
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.
authors.affiliation: a Division of Applied Science, Graduate School of Agriculture , Hokkaido University , Sapporo , Japan.
authors.forename: Lei
authors.initials: L
authors.lastname: Wang
authors.forename: Yuta
authors.initials: Y
authors.lastname: Murai
authors.forename: Takuma
authors.initials: T
authors.lastname: Yoshida
authors.forename: Masashi
authors.initials: M
authors.lastname: Okamoto
authors.forename: Katsuyoshi
authors.initials: K
authors.lastname: Masuda
authors.forename: Yasuko
authors.initials: Y
authors.lastname: Sakihama
authors.forename: Yasuyuki
authors.initials: Y
authors.lastname: Hashidoko
authors.forename: Yasumaru
authors.initials: Y
authors.lastname: Hatanaka
authors.forename: Makoto
authors.initials: M
authors.lastname: Hashimoto
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D003903:Deuterium / Q000737:chemistry*; D041961:Deuterium Exchange Measurement; D008698:Mesylates / Q000737:chemistry*; D013696:Temperature
chemical_list: D000596:Amino Acids; D008698:Mesylates; D003903:Deuterium; C012077:trifluoromethanesulfonic acid
keywords: Hydrogen/deuterium exchange; aromatic α-amino acid; cross-link; photophore; triflic acid