Abstract
Various types of amino-reductones are known to be involved in process-induced chemical changes in foods. Since most amino-reductones, especially enaminol compounds are unstable reaction intermediates and are difficult to isolate, their structural characteristics are still unclear. In order to obtain more precise structural information about amino-reductones, the structures of the enaminol form of fructoseglysine (D-fructoseglycine = FG) and scorbamic acid (L-scorbamic acid = SCA), a relatively stable cyclic enaminol compound were examined by the use of a semi-empirical molecular orbital method. Optimized structures, heat of formations and charge distributions of various enol forms of FG were obtained. Heat of formations of the non-dissociated, mono-anion, and di-anion forms of FG were estimated to be about-302,-347 and-308 kcal/mol, respectively. Optimized structures of non-dissociated, anion, and dipolar ion forms of SCA were also obtained and their heat of formations were estimated to be about-197,-204 and-248 kcal/mol, respectively. The nitrogen atom of the enaminol group in the SCA molecule was found to be positively charged.
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Kurata, T., Otsuka, Y. (1998). Amino-Reductones. In: Shahidi, F., Ho, CT., van Chuyen, N. (eds) Process-Induced Chemical Changes in Food. Advances in Experimental Medicine and Biology, vol 434. Springer, Boston, MA. https://doi.org/10.1007/978-1-4899-1925-0_22
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DOI: https://doi.org/10.1007/978-1-4899-1925-0_22
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