2-Aminoethyl phosphonic acid

The conversion of carboxyphosphonoenolpyruvate (CPEP) (164) into phosphinopyruvate (165) has been shown to be catalyzed by a CPEP phosphonomutase.Phosphoenolpyruvate(PEP)-phosphomutase is another enzyme which also catalyzes C-P bond formation and appears to play a central role in the biosynthesis of (2-aminoethyl)phosphonic acid. Possible mechanisms for the formation of the C-P bond under biological conditions through this latter role have been considered... 

Hammerschmidt, F., Biosynthesis of natural products with a P-C bond. Part 1. Incorporation of D-[6,6-D2]glucose into (2-aminoethyl)phosphonic acid in Tetrahymena thermophila, Liebigs Ann. Chem., 531, 1988. 

Aminoethylphosphonate.—n.m.r. measurements indicate that 78% of the phosphorus present in a water-soluble glycoprotein from the sea anemone Metridium dianthus is in the phosphonate form and includes 2-aminoethyl-phosphonic acid (20). N.m.r. for the identification of naturally occurring phosphonates appears to be a technique superior to chromatography, which has been used hitherto. ... 

Aminoethyl)phosphonic acid (AEP) has been prepared, together with other (u-aminoalkyl)phosphonic acids, by the borane-Me2S reduction of oo-(dialkoxyphosphiny 1) carboxamides, and also via its N,0,0-tris(trimethylsilyl) derivative (248) obtained from an N-acylaziridine. 

Aminoethyl)phosphonic acid (5) occurs as various V-substituted derivatives in several lower organisms Compounds 6", 7 and 8, are all antibiotics. Further details of these compounds can be found in ref. 18. 

Aminophosphonic acids play an important role in living systems. The first acid to be found naturally, namely (2-aminoethyl)phosphonic acid (also known as ciliatine, 2AEPH, and jS-Ala ) , has been followed more recently by 2-amino-5-phosphonopent-2-enoic acid, isolated from Streptomyces plumbens, and (2-amino-l-hydroxyethyl)phosphonic acid, isolated from Acanthamoeba castellani and formed through the biological hydroxylation of (2-aminoethyl)phosphonic acid. Many acids are inhibitors of enzymes important in carboxylic acid biochemistry. Ala is a potent inhibitor of a racemase from Gram-positive bacteria (the corresponding phosphinic acid 99 is not). Phosphinothricin... 

In an application of the Hofmann reaction, triethyl 3-phosphonopropanoate [ethyl 3-(diethoxyphosphinoyl)propanoate] was converted into (2-aminoethyl)phosphonic acid, but phosphinoyl carboxamides are also reduced to the amine without loss of carbon through the use of BH3 SMe2 in thf at 0 The Schmidt reaction was employed in a syn-... 

The anion from (cyanomethyl)phosphonic bis(dimethylamide) (331 R = R = H) may be mono- or di-alkylated, and the products sequentially reduced with H2-Raney nickel and hydrolysed under acidic conditions to give (2-aminoethyl)phosphonic acid or its C(i) alkylated derivatives. In the search for simple procedures which might lead to better asymmetric induction and so provide products of reasonable optical purity, the... 

Aminoethyl phosphonic acid most common naturally occurring phosphonate, found in a variety of organisms. 

The synthesis of DAAmEP was conducted in three steps. The first step was a Michaelis-Arhuzov reaction between N-(2-bromoethyl)phthalimide and an excess of triethyl phosphite under reflux at 160 °C for 12 h. In the second step, the reaction between the resulting phthalimide and hydrazine led to the formation of (2-aminoethyl)phosphonic acid diethyl ester. The final step consisted of the reaction between the actyloyl chloride and the diethyl ester, which was achieved in the presence of poly(4-vinylpyridine), 2% crosslinked, to trap the hydrochloric acid produced during the acryloylation. The final DAAmEP monomer was obtained after purification by chromatography on silica gel. All intermediate products were characterized by H and P NMR. The H NMR spectrum of the DAAmEP monomer allowed validation of the expected chemical structure and as a consequence the synthetic pathway. RAFT homopolymerization of DAAmEP was carried out with two different trithiocarbonate chain transfer agents (see Scheme 2.6). 

Mttredge, J.S., Roberts, E., and Simonsen, D.G. (1962) The occurrence of free 2-aminoethyl-phosphonic acid in the sea anemone Anthopleura elegantissima. Biochemistry, 1, 624—628. 

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