Origins of Life and Evolution of Biospheres

, Volume 48, Issue 4, pp 395–406 | Cite as

Chiral Recognition in Cold Gas-Phase Cluster Ions of Carbohydrates and Tryptophan Probed by Photodissociation

  • Doan Thuc Nguyen
  • Akimasa FujiharaEmail author
Prebiotic Chemistry, Chirality


Chiral recognition between tryptophan (Trp) and carbohydrates such as d-glucose (d-Glc), methyl-α-d-glucoside (d-glucoside), d-maltose, and d-cellobiose in cold gas-phase cluster ions was investigated as a model for chemical evolution in interstellar molecular clouds using a tandem mass spectrometer containing a cold ion trap. The photodissociation mass spectra of cold gas-phase clusters that contained Na+, Trp enantiomers, and d-maltose showed that Na+(d-Glc) was formed via the glycosidic bond cleavage of d-maltose from photoexcited homochiral Na+(d-Trp)(d-maltose), while the dissociation did not occur in heterochiral Na+(l-Trp)(d-maltose). The enantiomer-selective dissociation was also observed in the case of d-cellobiose. The enantiomer-selective glycosidic bond cleavage of disaccharides suggested that photoexcited d-Trp could prevent chemical evolution of sugar chains from d-enantiomer of carbohydrates in molecular clouds. The spectra of gas-phase clusters that contained Na+, Trp enantiomers, and d-Glc indicated that enantiomer-selective protonation of l-Trp from d-Glc could induce enantiomeric excess via collision-activated dissociation of the protonated l-Trp. In the case of protonated clusters, photoexcited H+(l-Trp) dissociated via Cα–Cβ bond cleavage in the presence of d-Glc or d-glucoside, where the excited states of H+(l-Trp) contributed to the enantiomer-selective reaction in the clusters. These enantiomer selectivities in cold gas-phase clusters indicated that chirality of a molecule induced enantiomeric excess of other molecules via enantiomer-selective reactions in molecular clouds.


Chemical evolution Molecular cloud Enantiomer Chirality Mass spectrometry 



This work was supported by JSPS KAKENHI Grant Number 17 K14441.

Compliance with Ethical Standards

Conflict of Interest



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© Springer Nature B.V. 2019

Authors and Affiliations

  1. 1.Department of Chemistry, Graduate School of ScienceOsaka Prefecture UniversityOsakaJapan

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