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

Olga S Soficheva 1
Olga S Soficheva
, 
Alina A Nesterova 1, 2
Alina A Nesterova
, 
Alexey Borisovich Dobrynin 1
Alexey Borisovich Dobrynin
, 
Ekaterina Mikhailovna Zueva 1, 3
Ekaterina Mikhailovna Zueva
, 
Joachim W Heinicke 4
Joachim W Heinicke
,  , 
Dmitry Grigorievich Yakhvarov 1, 2
Dmitry Grigorievich Yakhvarov
10.1016/j.mencom.2020.07.038
Published 2020-06-26
Communication , Volume 30, Issue 4, 516-518
6
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Soficheva O. S. et al. The effect of N-substituent on the relative thermodynamic stability of unionized and zwitterionic forms of α-diphenylphosphino-α-amino acids // Mendeleev Communications. 2020. Vol. 30. No. 4. pp. 516-518.
GOST all authors (up to 50) Copy
Soficheva O. S., Nesterova A. A., Dobrynin A. B., Zueva E. M., Heinicke J. W., Sinyashin O. G., Yakhvarov D. G. The effect of N-substituent on the relative thermodynamic stability of unionized and zwitterionic forms of α-diphenylphosphino-α-amino acids // Mendeleev Communications. 2020. Vol. 30. No. 4. pp. 516-518.
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TY - JOUR
DO - 10.1016/j.mencom.2020.07.038
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.07.038
TI - The effect of N-substituent on the relative thermodynamic stability of unionized and zwitterionic forms of α-diphenylphosphino-α-amino acids
T2 - Mendeleev Communications
AU - Soficheva, Olga S
AU - Nesterova, Alina A
AU - Dobrynin, Alexey Borisovich
AU - Zueva, Ekaterina Mikhailovna
AU - Heinicke, Joachim W
AU - Sinyashin, Oleg Gerol'dovich
AU - Yakhvarov, Dmitry Grigorievich
PY - 2020
DA - 2020/06/26
PB - Mendeleev Communications
SP - 516-518
IS - 4
VL - 30
ER -
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@article{2020_Soficheva,
author = {Olga S Soficheva and Alina A Nesterova and Alexey Borisovich Dobrynin and Ekaterina Mikhailovna Zueva and Joachim W Heinicke and Oleg Gerol'dovich Sinyashin and Dmitry Grigorievich Yakhvarov},
title = {The effect of N-substituent on the relative thermodynamic stability of unionized and zwitterionic forms of α-diphenylphosphino-α-amino acids},
journal = {Mendeleev Communications},
year = {2020},
volume = {30},
publisher = {Mendeleev Communications},
month = {Jun},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.07.038},
number = {4},
pages = {516--518},
doi = {10.1016/j.mencom.2020.07.038}
}
MLA
Cite this
MLA Copy
Soficheva, Olga S., et al. “The effect of N-substituent on the relative thermodynamic stability of unionized and zwitterionic forms of α-diphenylphosphino-α-amino acids.” Mendeleev Communications, vol. 30, no. 4, Jun. 2020, pp. 516-518. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.07.038.

Keywords

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

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.

References

8.
Crystal structure studies of amino acids and peptides.
Marsh R.E., Donohue J.
Advances in Protein Chemistry, 1967
10.
Bioconjugation and Active Site Design of Enzymes Using Non-natural Amino Acids
Kwon I., Yang B.
Industrial & Engineering Chemistry Research, 2017
11.
Recent advances in the synthesis and application of fluorescent α-amino acids
Harkiss A.H., Sutherland A.
Organic and Biomolecular Chemistry, 2016
12.
Peptidomimetics via modifications of amino acids and peptide bonds
Avan I., Hall C.D., Katritzky A.R.
Chemical Society Reviews, 2014
14.
10.1016/j.mencom.2020.07.038_sbref0020e
Hicks
Unnatural Amino Acids: Methods and Protocols, 2012
15.
Employing Unnatural Amino Acids in the Preparation of Biooconjugates
Young D., Maza J., Jacobs T., Uthappa D.
Synlett, 2016
16.
Amino acid modified Ni catalyst exhibits reversible H 2 oxidation/production over a broad pH range at elevated temperatures
Dutta A., DuBois D.L., Roberts J.A., Shaw W.J.
Proceedings of the National Academy of Sciences of the United States of America, 2014
17.
Dual properties of a hydrogen oxidation Ni-catalyst entrapped within a polymer promote self-defense against oxygen
Oughli A.A., Ruff A., Boralugodage N.P., Rodríguez-Maciá P., Plumeré N., Lubitz W., Shaw W.J., Schuhmann W., Rüdiger O.
Nature Communications, 2018
18.
Electrocatalytic Oxidation of Formate with Nickel Diphosphine Dipeptide Complexes: Effect of Ligands Modified with Amino Acids
Galan B.R., Reback M.L., Jain A., Appel A.M., Shaw W.J.
European Journal of Inorganic Chemistry, 2013
19.
Photoswitching a molecular catalyst to regulate CO2 hydrogenation
Priyadarshani N., Ginovska B., Bays J.T., Linehan J.C., Shaw W.J.
Dalton Transactions, 2015
20.
Chemistry of α‐Phosphanyl α‐Amino Acids
Peulecke N., Yakhvarov D.G., Heinicke J.W.
European Journal of Inorganic Chemistry, 2018
21.
Novel α-functionally substituted amino acids: diphenylphosphinoglycines
Heinicke J., Peulecke N., Jones P.G.
Chemical Communications, 2005
22.
α-Phosphanyl amino acids: synthesis, structure and properties of alkyl and heterocyclic N-substituted diphenylphosphanylglycines
Lach J., Peulecke N., Kindermann M.K., Palm G.J., Köckerling M., Heinicke J.W.
Tetrahedron, 2015
23.
α-Phosphanyl Amino Acids: Synthesis, Structure and Reactivity of N-Aryl-α-phosphanylglycines
Lach J., Guo C., Kindermann M.K., Jones P.G., Heinicke J.
European Journal of Organic Chemistry, 2010
24.
J. Lach, PhD Thesis, Greifswald, 2009.
25.
10.1016/j.mencom.2020.07.038_sbref0050a
Fomina
Uch. Zap. Kazan. Univ., Ser. Estestv. Nauki, 2012
26.
α-Phosphanyl amino acids: Diphenylphosphanyl glycines with a chiral N-substituent
Lach J., Peulecke N., Jones P.G., Dix I., Heinicke J.W.
Polyhedron, 2016
27.
Soficheva O.S., Bekmukhamedov G.E., Dobrynin A.B., Heinicke J.W., Sinyashin O.G., Yakhvarov D.G.
Mendeleev Communications, 2019
28.
Electrochemical Properties of N-Substituted α-Diphenylphosphinoglycines
Soficheva O.S., Kislitsyn Y.A., Nesterova A.A., Dobrynin A.B., Yakhvarov D.G.
Russian Journal of Electrochemistry, 2020
29.
APEX2, version 2.1, SAINTPlus, Data Reduction and Correction Program, version 7.31A, Bruker Advanced X-ray Solutions, Bruker AXS, Madison, WI, USA, 2006.
30.
G. M. Sheldrick, SADABS, Program for Empirical X-ray Absorption Correction, Bruker-Nonius, 1990-2004.
31.
10.1016/j.mencom.2020.07.038_bib0075
Sheldrick
Acta Crystallogr., 2015
32.
WinGXsuite for small-molecule single-crystal crystallography
Farrugia L.J.
Journal of Applied Crystallography, 1999
33.
10.1016/j.mencom.2020.07.038_bib0085
Spek
Acta Crystallogr., 2009
34.
Mercury CSD 2.0– new features for the visualization and investigation of crystal structures
Macrae C.F., Bruno I.J., Chisholm J.A., Edgington P.R., McCabe P., Pidcock E., Rodriguez-Monge L., Taylor R., van de Streek J., Wood P.A.
Journal of Applied Crystallography, 2008