Polypeptide formation in clusters of β-alanine amino acids by single ion impact.
Journal
Nature communications
ISSN: 2041-1723
Titre abrégé: Nat Commun
Pays: England
ID NLM: 101528555
Informations de publication
Date de publication:
30 07 2020
30 07 2020
Historique:
received:
04
02
2020
accepted:
01
07
2020
entrez:
1
8
2020
pubmed:
1
8
2020
medline:
9
9
2020
Statut:
epublish
Résumé
The formation of peptide bonds by energetic processing of amino acids is an important step towards the formation of biologically relevant molecules. As amino acids are present in space, scenarios have been developed to identify the roots of life on Earth, either by processes occurring in outer space or on Earth itself. We study the formation of peptide bonds in single collisions of low-energy He
Identifiants
pubmed: 32732937
doi: 10.1038/s41467-020-17653-z
pii: 10.1038/s41467-020-17653-z
pmc: PMC7393107
doi:
Substances chimiques
Amino Acids
0
Dipeptides
0
Ions
0
Oligopeptides
0
Peptides
0
Water
059QF0KO0R
beta-Alanine
11P2JDE17B
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
3818Références
Merrifield, R. B. Solid phase peptide synthesis. I. The synthesis of a tetrapeptide. J. Am. Chem. Soc. 85, 2149–2154 (1963).
doi: 10.1021/ja00897a025
Jones, J. H. In Major Methods of Peptide Bond Formation, Vol. 1. (eds Gross, E., Meienhofer, J.) 65–104 (Academic Press, 1979).
Seebach, D. & L.Matthews, J. β -Peptides: a surprise at every turn. Chem. Commun. 1997, 2015–2022 (1997).
doi: 10.1039/a704933a
Oró, J. Comets and the formation of biochemical compounds on the primitive earth. Nature 190, 389–390 (1961).
doi: 10.1038/190389a0
Ehrenfreund, P., Spaans, M. & Holm, N. G. The evolution of organic matter in space. Philos. Trans. R. Soc. A: Math., Phys. Eng. Sci. 369, 538–554 (2011).
doi: 10.1098/rsta.2010.0231
Herbst, E. & van Dishoeck, E. F. Complex organic interstellar molecules. Annu. Rev. Astron. Astrophys. 47, 427–480 (2009).
doi: 10.1146/annurev-astro-082708-101654
Schmitt-Kopplin, P. et al. High molecular diversity of extraterrestrial organic matter in Murchison meteorite revealed 40 years after its fall. Proc. Natl Acad. Sci. USA 107, 2763–2768 (2010).
doi: 10.1073/pnas.0912157107
Lodders, K. & Osborne, R. Perspectives on the comet-asteroid-meteorite link. Space Sci. Rev. 90, 289–297 (1999).
doi: 10.1023/A:1005226921031
Ehrenfreund, P., Glavin, D. P., Botta, O., Cooper, G. & Bada, J. L. Extraterrestrial amino acids in Orgueil and Ivuna: tracing the parent body of CI type carbonaceous chondrites. Proc. Natl Acad. Sci. USA 98, 2138–2141 (2001).
doi: 10.1073/pnas.051502898
Bernstein, M. P., Dworkin, J. P., Sandford, S. A., Cooper, G. W. & Allamandola, L. J. Racemic amino acids from the ultraviolet photolysis of interstellar ice analogues. Nature 416, 401–403 (2002).
doi: 10.1038/416401a
Meinert, C. et al. N-(2-Aminoethyl)glycine and amino acids from interstellar ice analogues. ChemPlusChem 77, 186–191 (2012).
Öberg, K. I. Photochemistry and astrochemistry: photochemical pathways to interstellar complex organic molecules. Chem. Rev. 116, 9631–9663 (2016).
doi: 10.1021/acs.chemrev.5b00694
Wollin, G. & Ericson, D. B. Amino-acid synthesis from gases detected in interstellar space. Nature 233, 615–616 (1971).
doi: 10.1038/233615a0
Blagojevic, V., Petrie, S. & Bohme, D. K. Gas-phase syntheses for interstellar carboxylic and amino acids. Monthly Not. R. Astronomical Soc. 339, L7–L11 (2003).
doi: 10.1046/j.1365-8711.2003.06351.x
Malar, E. J. P. & Divya, P. Structural stability in dimer and tetramer clusters of l-alanine in the gas phase and the feasibility of peptide bond formation. J. Phys. Chem. B 122, 6462–6470 (2018).
doi: 10.1021/acs.jpcb.8b01629
Van Dornshuld, E., Vergenz, R. A. & Tschumper, G. S. Peptide bond formation via glycine condensation in the gas phase. J. Phys. Chem. B 118, 8583–8590 (2014).
doi: 10.1021/jp504924c
Czapla, M. & Freza, S. Uncatalyzed peptide bond formation between two double amino acid molecules in the gas phase. Int. J. Quantum Chem. 117, e25435 (2017).
doi: 10.1002/qua.25435
Redondo, P., Martínez, H., Cimas, A., Barrientos, C. & Largo, A. Computational study of peptide bond formation in the gas phase through ion-molecule reactions. Phys. Chem. Chem. Phys. 15, 13005–13012 (2013).
doi: 10.1039/c3cp51535d
McGee, W. M. & McLuckey, S. A. Efficient and directed peptide bond formation in the gas phase via ion/ion reactions. Proc. Natl Acad. Sci. USA 111, 1288–1292 (2014).
doi: 10.1073/pnas.1317914111
Peng, Z. & McLuckey, S. A. C-terminal peptide extension via gas-phase ion/ion reactions. Int. J. Mass Spectrom. 391, 17–23 (2015).
doi: 10.1016/j.ijms.2015.07.027
Singh, A., Kaur, S., Kaur, J. & Singh, P. Transformation of gas-phase amino acid clusters to dipeptides: a nice approach to demonstrate the formation of prebiotic peptides. Rapid Commun. Mass Spectrom. 28, 2019–2023 (2014).
doi: 10.1002/rcm.6985
Lee, S., Valentine, S. J., Reilly, J. P. & Clemmer, D. E. Controlled formation of peptide bonds in the gas phase. J. Am. Chem. Soc. 133, 15834–15837 (2011).
doi: 10.1021/ja205471n
Lee, S., Julian, R. R., Valentine, S. J., Reilly, J. P. & Clemmer, D. E. Biomolecular condensation via ultraviolet excitation in vacuo. Int. J. Mass Spectrom. 316-318, 6–11 (2012).
doi: 10.1016/j.ijms.2012.02.015
Lee, S., Glover, M. S., Reilly, J. P. & Clemmer, D. E. Photosynthesis of a combinatorial peptide library in the gas phase. Anal. Chem. 87, 9384–9388 (2015).
doi: 10.1021/acs.analchem.5b02179
Zettergren, H. et al. Magic and hot giant fullerenes formed inside ion irradiated weakly bound C
doi: 10.1063/1.3479584
Delaunay, R. et al. Molecular growth inside of polycyclic aromatic hydrocarbon clusters induced by ion collisions. J. Phys. Chem. Lett. 6, 1536–1542 (2015).
doi: 10.1021/acs.jpclett.5b00405
Delaunay, R. et al. Shock-driven formation of covalently bound carbon nanoparticles from ion collisions with clusters of C
doi: 10.1016/j.carbon.2017.12.079
Capron, M. et al. A Multicoincidence study of fragmentation dynamics in collision of γ -aminobutyric acid with low-energy ions. Chem. - A Eur. J. 18, 9321–9332 (2012).
doi: 10.1002/chem.201103922
Maclot, S. et al. Dynamics of glycine dications in the gas phase: ultrafast intramolecular hydrogen migration versus Coulomb repulsion. J. Phys. Chem. Lett. 4, 3903–3909 (2013).
doi: 10.1021/jz4020234
Piekarski, D. G. et al. Unusual hydroxyl migration in the fragmentation of β-alanine dication in the gas phase. Phys. Chem. Chem. Phys. 17, 16767–16778 (2015).
doi: 10.1039/C5CP01628B
Maclot, S. et al. Determination of energy-transfer distributions in ionizing ion-molecule collisions. Phys. Rev. Lett. 117, 073201 (2016).
doi: 10.1103/PhysRevLett.117.073201
Piekarski, D. G. et al. Production of doubly-charged highly reactive species from the long-chain amino acid GABA initiated by Ar
doi: 10.1039/C7CP00903H
Piekarski, D. G. & Díaz-Tendero, S. Structure and stability of clusters of β -alanine in the gas phase: importance of the nature of intermolecular interactions. Phys. Chem. Chem. Phys. 19, 5465–5476 (2017).
doi: 10.1039/C6CP07792G
Martinet, G. et al. Fragmentation of highly excited small neutral carbon clusters. Phys. Rev. Lett. 93, 063401 (2004).
doi: 10.1103/PhysRevLett.93.063401
Bernigaud, V. et al. ARIBE: a low-energy ion beam facility in Caen. Publ. Astronomical Observatory Belgrade 84, 83–86 (2008).
Bergen, T. et al. Multiply charged cluster ion crossed-beam apparatus: multi-ionization of clusters by ion impact. Rev. Sci. Instrum. 70, 3244–3253 (1999).
doi: 10.1063/1.1149900
Chandezon, F., Huber, B. A. & Ristori, C. A new regime Wiley-McLaren time-of-flight mass spectrometer. Rev. Sci. Instrum. 65, 3344–3353 (1994).
doi: 10.1063/1.1144571
TURBOMOLE V6.2 2010, a development of University of Karlsruhe and Forschungszentrum Karlsruhe GmbH, 1989-2007, TURBOMOLE GmbH; http://www.turbomole.com (2007).
Frisch, M. J. et al. Gaussian 09 Revision E.01 (Gaussian Inc., Wallingford, CT, 2009).
Zhao, Y. & Truhlar, D. G. The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals. Theor. Chem. Acc. 120, 215–241 (2008).
doi: 10.1007/s00214-007-0310-x