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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 & Biomolecular Chemistry, 2010; 8(21):4934-4939
Publisher: Royal Soc Chemistry
Issue Date: 2010
ISSN: 1477-0520
Statement of
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
RMID: 0020101101
DOI: 10.1039/c0ob00232a
Appears in Collections:Chemistry and Physics publications

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