Ab initio calculation of the carbon isotope signatures of amino acids

Carbon isotope compositions for the 20 standard amino acids are calculated using high-level molecular orbital and density functional theory methods. In agreement with measurements of the isotopic compositions of amino acids in a cyanobacterium Macko, S.A., Fogel, M.L., Hare, P.E., Hoering, T.C., 1987. Isotope fractionation of nitrogen and carbon in the synthesis of amino acids by microorganisms. Chemical Geology 65, 79–92] the calculations give heavy signatures for aspartic acid + asparagine, serine, glutamine + glutamic acid and light signatures for leucine and isoleucine. The relative intramolecular enrichment of ¹³C in carboxyl groups is often much less than measured Abelson, P.H., Hoering, T.C., 1961. Carbon isotope fractionation in formation of amino acids by photosynthetic organisms. Proceedings of the National Academy of Sciences, USA 47, 623–632]. Fractionations predicted from density functional calculations often differ by several per mil from those predicted from molecular orbital calculations.