1-(Acylamino)alkylphosphonic Acids—Alkaline Deacylation
AbstractThe 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
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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.
Cypryk M, Drabowicz J, Gostynski B, Kudzin MH, Kudzin ZH, Urbaniak P. 1-(Acylamino)alkylphosphonic Acids—Alkaline Deacylation. Molecules. 2018; 23(4):859.Chicago/Turabian Style
Cypryk, Marek; Drabowicz, Jozef; Gostynski, Bartlomiej; Kudzin, Marcin H.; Kudzin, Zbigniew H.; Urbaniak, Pawel. 2018. "1-(Acylamino)alkylphosphonic Acids—Alkaline Deacylation." Molecules 23, no. 4: 859.
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