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- Title
Enantioselective Collision-Activated Dissociation of Gas-Phase Tryptophan Induced by Chiral Recognition of Protonated l-Alanine Peptides.
- Authors
Fujihara, Akimasa; Matsuyama, Hiroki; Tajiri, Michiko; Wada, Yoshinao; Hayakawa, Shigeo
- Abstract
Enantioselective dissociation in the gas phase is important for enantiomeric enrichment and chiral transmission processes in molecular clouds regarding the origin of homochirality in biomolecules. Enantioselective collision-activated dissociation (CAD) of tryptophan (Trp) and the chiral recognition ability of l-alanine peptides ( l-Ala; n = 2-4) were examined using a linear ion trap mass spectrometer. CAD spectra of gas-phase heterochiral H( d-Trp)( l-Ala) and homochiral H( l-Trp)( l-Ala) noncovalent complexes were obtained as a function of the peptide size n. The HO-elimination product was observed in CAD spectra of both heterochiral and homochiral complexes for n = 2 and 4, and in homochiral H( l-Trp)( l-Ala), indicating that the proton is attached to the l-alanine peptide, and HO loss occurs from H( l-Ala) in the noncovalent complexes. HO loss did not occur in heterochiral H( d-Trp)( l-Ala), where NH loss and (HO + CO) loss were the primary dissociation pathways. In heterochiral H( d-Trp)( l-Ala), the protonation site is the amino group of d-Trp, and NH loss and (HO + CO) loss occur from H( d-Trp). l-Ala peptides recognize d-Trp through protonation of the amino group for peptide size n = 3. NH loss and (HO + CO) loss from H( d-Trp) proceeds via enantioselective CAD in gas-phase heterochiral H( d-Trp)( l-Ala) at room temperature, whereas l-Trp dissociation was not observed in homochiral H( l-Trp)( l-Ala). These results suggest that enantioselective dissociation induced by chiral recognition of l-Ala peptides through protonation could play an important role in enantiomeric enrichment and chiral transmission processes of amino acids.
- Subjects
GAS phase reactions; ALANINE; MASS spectrometry; PROTON transfer reactions; FRAGMENTATION reactions
- Publication
Origins of Life & Evolution of the Biosphere, 2017, Vol 47, Issue 2, p161
- ISSN
0169-6149
- Publication type
Article
- DOI
10.1007/s11084-016-9511-4