O. S. Soficheva, A. A. Nesterova, A. B. Dobrynin, E. M. Zueva, J. W. Heinicke, O. G. Sinyashin, D. G. Yakhvarov, “The effect of N-substituent on the relative thermodynamic stability of unionized and zwitterionic forms of α-diphenylphosphino-α-amino acids”, Mendeleev Commun., 2020, Volume 30, Issue 4,Pages <nobr>516

This article is cited in 7 papers

Communications

The effect of N-substituent on the relative thermodynamic stability of unionized and zwitterionic forms of α-diphenylphosphino-α-amino acids

O. S. Soficheva^a, A. A. Nesterova^ab, A. B. Dobrynin^a, E. M. Zueva^ac, J. W. Heinicke^d, O. G. Sinyashin^a, D. G. Yakhvarov^ab

^a A.E. Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of the Russian Academy of Sciences, Kazan, Russian Federation
^b A.M. Butlerov Chemistry Institute, Kazan Federal University, Kazan, Russian Federation
^c Kazan National Research Technological University, Kazan, Russian Federation
^d Institut fur Biochemie, Ernst-Moritz-Arndt Universitat Greifswald, Greifswald, Germany

Abstract: The relative thermodynamic stability of unionized and zwitterionic forms of α-phosphino-α-amino acids is governed by the substituent R at the nitrogen atom, namely, (het)aryl substituents favour the formation of the unionized form RHNCH(PPh₂)COOH, while in the case of alkyl analogues the zwitterions RH₂N⁺CH(PPh₂)COO⁻ predominate. The experimentally observed trends have been supported by quantum-chemical calculations. The synthesis and X-ray crystal structure analysis of a new unionized α-phosphino-α-amino acid [α-diphenylphosphino-N-(2-methoxycarbonylphenyl) glycine] are reported.

Keywords: amino acids, α-diphenylphosphino-α-amino acids, diphenylphosphinoglycines, unionized form, zwitterionic form, X-ray analysis, thermodynamic stability, quantum-chemical calculations.

Language: English

DOI: 10.1016/j.mencom.2020.07.038

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