Aminoethylphosphonic acid

C1SH19NO2 47017-04-9) see Metaraminol a-aminoethylphosphonic acid diethyl ester... 

A. Aminophosphonic Acids.— The Michael addition of a dialkyl phosphite to acrylonitrile leads to C—P bond formation and the production in high yield of derivatives of 2-aminoethylphosphonic acid (45). This synthetic method appears to be preferable to those already described. ... 

Ternan NG, JP Quinn (1998) Phosphate starvation-independent 2-aminoethylphosphonic acid biodegradation in a newly isolated strain of Pseudomonas putida, NG2. System Appl Microbiol 21 346-352. 

A new synthesis (Scheme 4) of 2-aminoethylphosphonic acid (24) has been described in which bis(dimethylamino) phosphorochloridate is condensed with an a-anion derived from an aliphatic nitrile.71 An advantage of this synthesis is that the intermediate (25) can be alkylated, which constitutes the simplest synthesis so far published for substituted aminoethylphosphonic acids. Both C-3 and the phosphorus atom of PEP are incorporated into (24) in Tetrahymena pyriformis,72 which confirms... 

Aminoalkylphosphonic acids are analogues of natural a-aminocarboxylic acids and are designated by generally accepted three-letter abbreviations for the amino acid residue followed by a superscript P. For example, 1-aminoethylphosphonic acid, which is related to alanine, is abbreviated as Alap. Diphenyl [l-(benzyloxycarbonylamino)ethyl]phosphonate, is abbreviated as Z-Alap(OPh)2. The l-aminoalkylphosphonic acids have modest water solubility, which significantly increases in strong acidic and alkali solution. They are not soluble... 

As seen in Scheme 1 a route similar to the biological pathway has now been explored by the independent synthesis of each precursors by chemical means. Work presented in this communication describes the production of synthetic 2-aminoethylphosphonic acids by the controlled reductive amination of 2-oxoalkylphosphonate diesters... 

N-Hydroxysuccinimide ester of N-benzyloxycarbonyl-L-alanine (lR,S)-l-Aminoethylphosphonic acid Benzylamine Palladium on carbon... 

Rosenburg, H. 1964. Distribution and fate of 2-aminoethylphosphonic acid in Tetrahymena. Nature (London) 203 299-300. 

Few papers have appeared during the past year which have dealt with naturally occurring phosphonates. A diacylglyceryl ester of 2-aminoethylphosphonic acid (17)... 

Imai. S., Seto, H., Ogawa, H., Satoh, A., and Otake, N., Studies on the biosynthesis of fosfomycin. Conversion of 2-hydroxyethylphosphonic acid and 2-aminoethylphosphonic acid to fosfomycin, Agric. Biol. Chem., 49, 873. 1985. 

Hammerschmidt, E, and Kahlig, H., Biosynthesis of natural products with a P-C bond. Part 10. Incorporation of D-[l- Hj]glucose into 2-aminoethylphosphonic acid in Tetrahymena thermophila and into fosfomycin in Streptomyces fradiae. The stereochemical course of a phosphoenolpyruvate mutase-catalyzed reaction, Liebigs Ann. Chem., 1201, 1992. 

Horignchi. M.. Biosynthesis of 2-aminoethylphosphonic acid in cell-free preparations from Tetrahymena, Biochim. Biophys. Acta, 261, 102, 1972. 

Kafarski, P., and Mastalerz, P., Synthesis of dipeptides containing P-terminal 2-aminoethylphosphonic acid, Rocz. Chem., 51, 433, 1977. 

The Hofmann degradation is applicable to the synthesis of 2-aminoalkylphosphonic acids." " For example, 2-aminoethylphosphonic acid has been obtained by this method in 75% yield (Scheme 8.94). To avoid the drastic conditions required by the hypobromite method, two new Hofmann-like reagents, iodosobenzene and /-hydroxy-Z-p-tolucnesulfonyloxyiodobcnzcnc (HTIB), have been introduced. Under these conditions, the rearrangement takes place smoothly to produce the desired aminoalkylphosphonic acids in high yields (65-93%). ... 

Barycki, J., Mastalerz, P, and Soroka, M., Simple synthesis of 2-aminoethylphosphonic acid and related compounds. Tetrahedron Lett., 11, 3147, 1970. 

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