EnantioselectivePhotolysis and Quantitative Chiral Analysis of Tryptophan Complexed With Alkali‐Metalized L‐Serine in the Gas Phase

Fujihara, Akimasa; Maeda, Naoto; Hayakawa, Shigeo

doi:10.1002/chir.22442

Cited by 10 publications

(3 citation statements)

References 26 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Trp, Phe, Tyr, and His contain indole, benzene, phenol, and imidazole side chains, respectively. Ser was formed by the ultraviolet irradiation of interstellar ice analogs [ 19 , 20 ], and showed enantiomer-selectivity in the gas phase [ 31 , 37 , 38 ]. Based on the results, we determined the amino-acid sequences of tripeptides needed for the recognition of aromatic amino acids.…”

Section: Introductionmentioning

confidence: 99%

Chiral and Molecular Recognition through Protonation between Aromatic Amino Acids and Tripeptides Probed by Collision-Activated Dissociation in the Gas Phase

et al. 2018

Self Cite

View full text Add to dashboard Cite

Chiral and molecular recognition through protonation was investigated through the collision-activated dissociation (CAD) of protonated noncovalent complexes of aromatic amino acid enantiomers with l-alanine- and l-serine-containing tripeptides using a linear ion trap mass spectrometer. In the case of l-alanine-tripeptide (AAA), NH3 loss was observed in the CAD of heterochiral H+(d-Trp)AAA, while H2O loss was the main dissociation pathways for l-Trp, d-Phe, and l-Phe. The protonation site of heterochiral H+(d-Trp)AAA was the amino group of d-Trp, and the NH3 loss occurred from H+(d-Trp). The H2O loss indicated that the proton was attached to the l-alanine tripeptide in the noncovalent complexes. With the substitution of a central residue of l-alanine tripeptide to l-Ser, ASA recognized l-Phe by protonation to the amino group of l-Phe in homochiral H+(l-Phe)ASA. For the protonated noncovalent complexes of His enantiomers with tripeptides (AAA, SAA, ASA, and AAS), protonated His was observed in the spectra, except for those of heterochiral H+(d-His)SAA and H+(d-His)AAS, indicating that d-His did not accept protons from the SAA and AAS in the noncovalent complexes. The amino-acid sequences of the tripeptides required for the recognition of aromatic amino acids were determined by analyses of the CAD spectra.

show abstract

Section: Introductionmentioning

confidence: 99%

Chiral and Molecular Recognition through Protonation between Aromatic Amino Acids and Tripeptides Probed by Collision-Activated Dissociation in the Gas Phase

et al. 2018

Self Cite

View full text Add to dashboard Cite

show abstract

“…[15] We have previously examined the UV photodissociation of cold gas-phase Trp enantiomers, both on a chiral crown ether and in L-serine clusters, as a model for interstellar molecular clouds. [16][17][18] This work indicated that enantioselective photodissociation of cold gas-phase amino acids on chiral substances by linearly polarized light could have played an important role in the origin of homochirality in biomolecules. This enantioselective photodissociation with linearly polarized light was applied to quantitative chiral analysis.…”

mentioning

confidence: 96%

“…The rate constants of two competitive dissociation pathways relate to the ion intensities of the product ions, and the natural logarithm plot was used for chiral recognition using mass spectrometry-based techniques. [8,9,11,18] A linear relationship for ln(R) versus the L-enantiomer fraction is obtained, with a slope of 1.867, an intercept of À1.078 and a correlation coefficient (r 2 ) of 0.989. This indicates that the optical purity of Trp can be determined by measuring the relative abundance ratio R in a photodissociation mass spectrum and by referring to the linear relationship shown in Fig.…”

mentioning

confidence: 99%

Chiral recognition between l‐alanine peptides and tryptophan enantiomers probed by ultraviolet photodissociation in the gas phase

2016

Self Cite

View full text Add to dashboard Cite

Chiral and molecular recognition of monosaccharides by photoexcited tryptophan in cold gas-phase noncovalent complexes as a model for chemical evolution in interstellar molecular clouds

Fujihara

Okawa

2018

Anal Bioanal Chem

View full text Add to dashboard Cite

Chiral and molecular recognition between amino acid and sugar molecules and their implications for chemical evolution were investigated using a tandem mass spectrometer equipped with an electrospray ionization source and a cold ion trap. Ultraviolet photodissociation of mass-selected and temperature-controlled gas-phase noncovalent complexes of protonated tryptophan (Trp) and monosaccharide enantiomers, such as aldohexose, aldopentose, and deoxyhexose, was examined as a model for chemical evolution in interstellar molecular clouds. Upon photoexcitation of noncovalent heterochiral H(L-Trp)(D-aldohexose) complexes, NHCHCOOH loss from protonated Trp via C-C bond cleavage occurred. Conversely, in homochiral H(L-Trp)(L-aldohexose), the energy absorbed by Trp was released through the detachment of aldohexose, and dissociation of the amino acid was suppressed. In the photodissociation mass spectra of protonated Trp with aldopentose and deoxyhexose, which lacks the OH group of aldohexose, no dissociation of the molecules in the complexes or differences between enantiomers were observed. These results indicate that the OH groups in monosaccharides contribute to enantiomer-selective photodissociation in molecular clouds. The differences observed between enantiomers in the photodissociation mass spectra were applied to distinguishing and quantifying aldohexose enantiomers in solution using L-Trp as a chiral probe. The enantiomeric excesses of aldohexoses in solution could be determined from a single photodissociation mass spectrum by reference to the relative ion intensities for the NHCHCOOH-elimination product and H(L-Trp) formed via detachment of aldohexose. This analysis method could also distinguish and quantify two D-aldohexose mixtures, where L-Trp was employed as an isomer probe. Graphical abstract ᅟ.

show abstract

EnantioselectivePhotolysis and Quantitative Chiral Analysis of Tryptophan Complexed With Alkali‐Metalized L‐Serine in the Gas Phase

Cited by 10 publications

References 26 publications

Chiral and Molecular Recognition through Protonation between Aromatic Amino Acids and Tripeptides Probed by Collision-Activated Dissociation in the Gas Phase

Chiral and Molecular Recognition through Protonation between Aromatic Amino Acids and Tripeptides Probed by Collision-Activated Dissociation in the Gas Phase

Chiral recognition between l‐alanine peptides and tryptophan enantiomers probed by ultraviolet photodissociation in the gas phase

Chiral and molecular recognition of monosaccharides by photoexcited tryptophan in cold gas-phase noncovalent complexes as a model for chemical evolution in interstellar molecular clouds

Contact Info

Product

Resources

About