Synthesis of phosphinothricine and other phosphorylic analogues of glutamic acid

Kurdyumova, N. R.; Ragulin, V. V.; Tsvetkov, E. N.

doi:10.1070/mc1997v007n02abeh000721

Cited by 18 publications

(15 citation statements)

References 9 publications

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“…ÄÄÄÄÄÄÄÄÄÄÄÄ Bis(triaminosilyl) hypophosphite (IV) is readily formed from ammonium hypophosphite (II) and silazane [19,20] and added in situ to ethyl acrylate to form bis(trimethylsilyl) 3-(ethoxycarbonyl)phopylphosphonite (V) [12]. Treatment of the latter in situ with excess 1,2-dibromoethane followed by alcoholysis gave (2-bromoethyl)-[2-(ethoxycarbonyl)ethyl]-phosphinic acid (VI) which was treated in situ with excess triethyl orthoformate.…”

Section: Imentioning

confidence: 99%

“…In this work we propose a new synthetic approach to pseudopeptides with reversed construction steps: The first phosphorus3carbon bond is formed via addition of a hypophosphite to an acrylate [12] and the second, by construction and addition of the aminoalkyl fragment [13]. This synthetic approach may prove more facile and convenient in one-pot formation of both phosphorus3carbon bonds, and we develop it aiming at preparing various functionally substituted phosphinic acids [14316].…”

mentioning

confidence: 99%

“…The proposed pseudo-g-glutamylpeptide synthesis is simplified by a convenient procedure [13,17,18] for preparing vinylphosphoryl compounds. The latter are used as starting materials for adding the amino acid function in the form of diethyl acetamidomalonate and forming a phosphoryl analog of glutaminic acid, viz.…”

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confidence: 99%

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Synthesis of phosphinic acids on the basis of hypophosphites: IV. Synthesis of pseudo-γ-glutamylglycine and its enantiomers

Ragulin

2004

Russ J Gen Chem

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Section: Imentioning

confidence: 99%

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Synthesis of phosphinic acids on the basis of hypophosphites: IV. Synthesis of pseudo-γ-glutamylglycine and its enantiomers

Ragulin

2004

Russ J Gen Chem

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“…These esters can be isolated pure as, for example, with aminophosphine oxide VIa or aminophosphinic acid VIf. [32] and ethyl (2-phenylethyl)(vinyl)phosphinate (IVc) [29] were prepared by a synthetic procedure we developed previously for vinylphophoryl compounds. The products were purified on Celite filter aid (Lancaster) and a mixture of silica gel L100/160 (Chemapol) with Brockmann neutral alumina (10320 weight %).…”

Section: äääääääääääämentioning

confidence: 99%

Phosphorus-containing Aminocarboxylic Acids: XIV. Synthesis of Analogs of α-Substituted Glutamic Acid

Saratovskikh

Ragulin

2005

Russ J Gen Chem

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Addition of Schiff bases derived from amino acid esters to appropriate vinylphosphoryl compounds, followed by hydrolysis of the adducts formed gives a series of new a-alkylated phosphorus-containing a-aminocarboxylic acids, viz. phosphonic and phosphinic analogs of glutamic acid.Synthesis of phosphoryl analogs of natural amino acids and peptides represents a prospective route to potential physiologically active compounds [237]. Substitution of the carbonyl group in a natural amino acid molecule by phosphoryl leads to aminophosphonic acids [234]. The key step in constructing aminophosphinic acid analogs of peptides involves substitution of the amide fragment C(O)NH by methylenephosphoryl CH 2 P(O) [537].Phosphorus-containing aminocarboxylic acids of general formula I possess diverse biological activity. Phosphonic analogs (X = Y = OH), such as 2-amino-4-phosphonobutyric acid (n = 2), and glutamic acid gomologs, such as 2-amino-5-phosphonovaleric (n = 3) and 2-amino-7-phosphonoheptanoic (n = 5) acids, are known as potent neuroprotectors [234].The modification of the carbon chain in [canonical] molecule I, including the synthesis of unsaturated analogs [8,9] and the introduction of aromatic [10,11], pyperidine [12], and piperazine [13,14] fragments, gave compounds with a high antispasmodic activity. Phosphinothricin, 2-amino-4-(methylphosphino)butyric acid (X = Me, Y = OH), the best phosphinic analog of glutamic acid, is glutaminsynthetase inhibitor and a highly active low-toxicity herbicide [15317]. Glutamic acid analogs and homologs bearing a phosphine oxide fragment have also been described [18]. Modification of the phosphorus-containing fragment and hydrocarbon chain in [canonical] ÄÄÄÄÄÄÄÄÄÄÄÄ 1 For communication XIII, see [1].molecule I is the most studied approach to constructing new phosphorus-containing aminocarboxylic acids [8320]. Over the past years, the physiologic activity of a-substituted phosphorus-containing a-aminocarboxylic acids, specifically a-methyl-4-phosphonophenylglycine and 2-amino-2-methyl-4-phosphonobutyric acids, as selective antagonists of metabotropic glutamate receptors has been reported [21323]. In this respect, modification of the aminocarboxylic fragment in molecule I can open up a prospective route in searching for new agonists and antagonists of metabotropic glutamate receptors, as well as potential inhibitors of natural enzymes in the series of phosphorus-containing aminocarboxylic acids [24326].This work is devoted to the synthesis of new wphosphorylated a-alkyl-a-aminocarboxylic acids II (Scheme 1) along Scheme 2. Phosphonic glutamic acid analogs IIb3IId are homologs of 2-amino-2-methyl-4-phosphonobutyric acid (IIa), and, therefore, they offer interest as potential antagonists and agonists of metabotropic glutamate receptors [21325]. Aminophosphonic acids with a hydroxycarbonylethyl fragment [IIf3IIh, X = OH, Y = CH 2 CH 2 C(O)OH] are phosphinic analogs of a-substituted g-glutamylglycines [6,7]. In this case, the role of pseudoglycine belongs to the propionic fragment, while...

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“…For comparison, we also studied the extraction with a neutral analog of II, pentaphenyldiethylenetriphosphine trioxide IV [6], and with diphenylphosphinic acid V. [7] and III [8] were prepared previously by the procedure based on our approach to synthesis of functionally substituted phosphinic acids from hypophosphites. The reaction of 2 equiv of 2-bromoethyldiphenylphosphine oxide with bis(trimethylsilyl) hypophosphite in situ allows preparation of symmetrical triphosphoryl-containing acid II by two successive reactions following the pattern of Arbuzov's rearrangement [7]. The successive reactions of styrene and then 2-bromoethyldiphenylphosphine oxide with bis(trimethylsilyl) hypophosphite in situ yield unsymmetrical diphosphoryl-containing acid III.…”

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Extraction Properties of Bis(diphenylphosphinylethyl)phosphinic Acid in Nitric Acid Solutions

2005

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Extraction of microamounts of U(VI), Th(IV), Sc(III), and Ln(III) from HNO 3 solutions with solutions of bis(diphenylphosphinylethyl)phosphinic acid in dichloroethane was studied. The stoichiometry of the extractable complexes was determined, and the effect of the inorganic anion and organic diluent on the extraction of rare-earth elements was examined. An increase in the number of phosphoryl groups in the extractant molecule and replacement of ethylene bridges between the phosphorus atoms by methylene bridges enhance the extraction of metal ions from nitric acid solutions.The interest in extraction properties of polyfunctional organophosphorus acids increased recently, because of the prospects for using these agents in radiochemical practice for the recovery of transplutonium, rare-earth (Ln), and other elements from nitric acid solutions [1]. It was shown that dibasic P, P`-di-(2-ethylhexyl)methylenediphosphonic acid [2, 3] and monobasic (diphenylphosphinylmethyl)phenylphosphinic [4] and bis(diphenylphosphinylmethyl)phosphinic (I) [5] acids exhibit extremely high extractive power toward Th(IV), U(VI), Am(III), and Ln(III) in nitric acid solutions. It was suggested that the high extractive power of acid I is due to the possibility of formation of six-membered chelate rings with metal ions, since the phosphoryl groups in this agent are linked with methylene bridges. In this connection, it is interesting to study how the length of the alkylene bridge between the P(O)OH and P(O) fragments and the number of phosphoryl groups in the extractant molecule affect its extractive power.To this end, we studied the extraction of U(VI), Th(IV), Sc(III), and Ln(III) from aqueous solutions of HNO 3 with solutions of bis(2-diphenylphosphinylethyl)phosphinic (II) and 2-phenylethyl-(2-diphenylphosphinylethyl)phosphinic (III) acids in dichloroethane. For comparison, we also studied the extraction with a neutral analog of II, pentaphenyldiethylenetriphosphine trioxide IV [6], and with diphenylphosphinic acid V.

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Synthesis of phosphinothricine and other phosphorylic analogues of glutamic acid

Cited by 18 publications

References 9 publications

Synthesis of phosphinic acids on the basis of hypophosphites: IV. Synthesis of pseudo-γ-glutamylglycine and its enantiomers

Synthesis of phosphinic acids on the basis of hypophosphites: IV. Synthesis of pseudo-γ-glutamylglycine and its enantiomers

Phosphorus-containing Aminocarboxylic Acids: XIV. Synthesis of Analogs of α-Substituted Glutamic Acid

Extraction Properties of Bis(diphenylphosphinylethyl)phosphinic Acid in Nitric Acid Solutions

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