1066-51-9Relevant articles and documents
Aminomethanephosphonic Acid and its Diphenyl Ester
Oleksyszyn, Jozef,Subotkowska, Lidia
, p. 906 (1980)
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Synthesis of 1-Phthalimidoalkanephosphonates
Baraldi, P. G.,Guarneri, M.,Moroder, F.,Pollini, G. P.,Simoni, D.
, p. 653 - 655 (1982)
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1-(Acylamino)alkylphosphonic acids—alkaline deacylation
Cypryk, Marek,Drabowicz, Jozef,Gostynski, Bartlomiej,Kudzin, Marcin H.,Kudzin, Zbigniew H,Urbaniak, Pawel
, (2018)
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.
Comments on the Synthesis of Aminomethylphosphonic Acid
Soroka, Miroslaw
, p. 547 - 548 (1989)
Two simple methods for the synthesis of aminomethylphosphonic acid from phosphorus(III) chloride and 1,3,5-triacylhexahydro-1,3,5-triazine or N-(hydroxymethyl)benzamide are described.
Chemical and Mutagenic Analysis of Aminomethylphosphonate Biodegradation
Avila, L. Z.,Loo, S. H.,Frost, J. W.
, p. 6758 - 6764 (1987)
Utilization of aminomethyl-, N-methylaminomethyl-, N,N-dimethylaminomethyl-, and N-acetylaminomethylphosphonate by Escherichia coli as a sole source of phosphorus during growth resulted in the extracellular generation of N-methylacetamide, N,N-dimethylacetamide, trimethylamine, and N-methylacetamide, respectively.Product identification relied on synthesis of (13)C-enriched aminomethylphosphonates followed by (1)H NMR analysis of products isolated from the biodegradation of the labeled and unlabeled phosphorus sources.To circumvent the requirement of an intact cell for carbon to phosphorus bond degradation, transposon mutagenesis was exploited as a complement to the chemical analysis.E. coli K-12 were infected with λTn5.Colonies resistant to kanamycin were selected and then screened for loss of the ability to use ethylphosphonate as a sole source of phosphorus.The mutant identified, E. coli SL724, was also unable to degrade aminomethylphosphonates.This combination of chemical and mutagenic analysis points toward a shared mechanism between alkyl- and aminomethylphosphonate biodegradation.
METHOD FOR THE SYNTHESIS OF AMINOALKYLENEPHOSPHONIC ACID
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Paragraph 0073, (2014/02/15)
The present invention is related to a method for the synthesis of an aminoalkylenephosphonic acid or its phosphonate esters comprising the following steps: a) forming, in the presence of an aldehyde or ketone and an acid catalyst, a reaction mixture by mixing a compound comprising at least one HNR1R2 moiety or a salt thereof, with a compound having one or more P-O-P anhydride moieties, said moieties comprising one P atom at the oxidation state (+III) and one P atom at the oxidation state (+III) or (+V), wherein the ratio of moles of aldehyde or ketone to N-H moieties is 1 or more and wherein the ratio of N-H moieties to P-O-P anhydride moieties is 0.3 or more and, b) recovering the resulting aminoalkylenephosphonic acid comprising compound or its phosphonate esters.
