2-Aminoethyl-phosphonic

The crystal structure of zinc phenylphosphonate was solved and demonstrated the anticipated layer structure with the phenyl rings occupying the interlamellar space.409 The structure of zinc ethylphosphonate and (2-aminoethyl)phosphonate both show four-coordinate zinc centers in contrast to the coordination number of six in the phenylphosphonate compound.410... 

Aminoethylarsonic acid, 44 220 N-(Aminoethyl) cyclam, preparation, 44 104 2-Aminoethyl phosphonate, bacterial breakdown, 44 206... 

The glycosphingolipids of marine invertebrates sometimes include groups unusual for this class of compound. Thus, in the glycolipids of gastropods, (2-aminoethyl)phosphonic and [2-(methylamino)ethyl]phosphonic groups... 

The phosphono form of phosphatidylethanolamine, 1,2-diacyl- n-glycerol-3-(2 -aminoethyl)phosphonate (Fig. 5), is present in several species of protozoa as well as in bovine tissues and in human aorta. Its alkylacyl and alkenylacyl forms have also been found. From the freshwater cyanobacteria Aphani-zomenon flos-aquae, 2-acyloxyethylphosphonate (with unusual biosurfactant properties) has been isolated. Phosphonolipids have been reviewed in References 36 and 37. 

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... 

B-alkylated derivatives of (2-aminoethyl)phosphonic diesters have... 

Mo,N,02 P2C,H2 5H2O, Pentamolybdobis-[(2-aminoethyl)phosphonate](4-), sodium tetramethylammonium dihydrogen, pentahydrate, 27 126 Mo,N402,P2C2H,2 2H20, Pentamo-... 

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... 

The reactions between Y-(co-haloalkyl)phthalimides and sodium dialkyl phosphite were reported as early as 1949 by Chavane in the successful sytheses of several (co-aminoalkyl)phosphonic diesters. The advantage over the Michaelis-Arbuzov reaction in the preparation of (2-aminoethyl)phosphonic diesters with Y-alkyl or Y-silvl substituents is worth recalling, and several reports of its successful use may be noted, including the preparation of nitrogen-functionalized polyphosphonic esters (Scheme 17). Other substrates for the reaction have included l,3-bis(bromomethyl)benzene and 4-(co-bromoalkyl)arenes ... 

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... 

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