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https://hdl.handle.net/2440/62834
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Type: | Journal article |
Title: | Radical formation of amino acid precursors in interstellar regions? Ser, Cys and Asp |
Author: | Knowles, D. Wang, T. Bowie, J. |
Citation: | Organic and Biomolecular Chemistry, 2010; 8(21):4934-4939 |
Publisher: | Royal Soc Chemistry |
Issue Date: | 2010 |
ISSN: | 1477-0520 1477-0539 |
Statement of Responsibility: | Daniel J. Knowles, Tianfang Wang and John H. Bowie |
Abstract: | It is proposed that the glycine precursor NH(2)CH(2)CN may be synthesised in interstellar dust clouds by the radical combination reactions NH(2)˙ + ˙CH(2)CN → NH(2)CH(2)CN (ΔG = -302 kJ mol(-1)) and/or NH(2)CH(2)˙ + ˙CN → NH(2)CH(2)CN (ΔG = -414 kJ mol(-1)). All calculations at the CCSD(T)/aug-cc-pVDZ//B3LYP/6-31+G(d) level of theory. This paper extends that concept to radical/radical coupling reactions to form Ser, Cys and Asp precursor nitriles. The hydrogen abstraction process NH(2)CH(2)CN + HO˙→ NH(2)˙CHCN + H(2)O (ΔG = -130 kJ mol(-1)) is suggested to precede the radical coupling reactions NH(2)˙CHCN + R˙→ NH(2)CHRCN (R˙ = ˙CH(2)OH, ˙CH(2)SH and ˙CH(2)CN) to form nitrile precursors of the amino acids Ser, Cys and Asp. These three reactions are all favourable (ΔG = -240, -227 and -223 kJ mol(-1)). The radical species ˙CH(2)NH(2), ˙CH(2)OH, ˙CH(2)SH and ˙CH(2)CN are shown to be stable for the microsecond timeframe by a combination of theoretical calculations and the experimental mass spectrometric neutralization/reionization procedure. |
Keywords: | Nitriles Cysteine Aspartic Acid Serine Thermodynamics |
Rights: | © The Royal Society of Chemistry 2010 |
DOI: | 10.1039/c0ob00232a |
Grant ID: | ARC |
Published version: | http://dx.doi.org/10.1039/c0ob00232a |
Appears in Collections: | Aurora harvest Chemistry and Physics publications |
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