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Molecules 2018, 23(4), 859; https://doi.org/10.3390/molecules23040859

1-(Acylamino)alkylphosphonic Acids—Alkaline Deacylation

1
Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 120a, Lodz 90-363, Poland
2
Department of Chemistry and Environment Protection, Jan Dlugosz University, Czestochowa 42-200, Poland
3
Textile Research Institute, Brzezinska 5/15, Lodz 92-103, Poland
4
Faculty of Chemistry, University of Lodz, Tamka 12, Lodz 91-403, Poland
*
Authors to whom correspondence should be addressed.
Academic Editor: György Keglevich
Received: 5 March 2018 / Revised: 26 March 2018 / Accepted: 28 March 2018 / Published: 9 April 2018
(This article belongs to the Special Issue Organophosphorus Chemistry 2018)
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Abstract

The alkaline deacylation of a representative series of 1-(acylamino)alkylphosphonic acids [(AC)-AAP: (AC) = Ac, TFA, Bz; AAP = GlyP, AlaP, ValP, PglP and PheP] in an aqueous solution of KOH (2M) was investigated. The results suggested a two-stage reaction mechanism with a quick interaction of the hydroxyl ion on the carbonyl function of the amide R-C(O)-N(H)- group in the first stage, which leads to instant formation of the intermediary acyl-hydroxyl adducts of R-C(O)2-N(H)-, visible in the 31P NMR spectra. In the second stage, these intermediates decompose slowly by splitting of the RC(O)2-N(H)- function with the subsequent formation of 1-aminoalkylphosphonate and carboxylate ions. View Full-Text
Keywords: amino acids; aminophosphonic acids; 1-aminoalkylphosphonic acids; 1-(acylamino)alkylphosphonic acids; 31P NMR spectra of intermediates; hydrolytic deacylation amino acids; aminophosphonic acids; 1-aminoalkylphosphonic acids; 1-(acylamino)alkylphosphonic acids; 31P NMR spectra of intermediates; hydrolytic deacylation
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).
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Cypryk, M.; Drabowicz, J.; Gostynski, B.; Kudzin, M.H.; Kudzin, Z.H.; Urbaniak, P. 1-(Acylamino)alkylphosphonic Acids—Alkaline Deacylation. Molecules 2018, 23, 859.

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