ChemInform Abstract: 1,2‐Phosphorylated Aziridines.

Gubnitskaya, E. S.; Peresypkina, L. P.; Iksanova, S. V.; Samarai, L. I.

doi:10.1002/chin.199052246

Cited by 2 publications

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“…Findings of AEP structural elements in various living organisms have stimulated active developments in this area. At present there are several general strategies to synthesize b-aminophosphonates, which are based on formation of PÀC, CÀC, and CÀN bonds or transformation of precursors [144,145].…”

Section: Synthesis Of B-aminophosphonatesmentioning

confidence: 99%

Chemistry of Aminophosphonic Acids and Phosphonopeptides

Kukhar

Romanenko

2009

Amino Acids, Peptides and Proteins in Organic Chemistry

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Aminophosphonic (and aminophosphinic) acids occupy a prominent position in the understanding of bioprocesses in living organisms and in the construction of new bioregulators -pharmaceuticals and agrochemicals. The so-called phosphorus analogs of the amino acids, aminophosphonic and aminophosphinic acids, are amino acid mimetics in which the carboxylic group is substituted by a phosphonic acid residue P(O)(OH) 2 or phosphinic acid group P(O)(OH)R. The replacement of the carboxylic group by a phosphonic or related moiety results in a number of important consequences: the central atom of a phosphonic acid function consists of an additional substituent that has a tetrahedral configuration in contrast to the planar carbonyl atom of carboxylic group. There are also significant differences in the acidity and steric bulk of these residues. The tetrahedral configuration of the pentavalent phosphorus atom mimics the transition state of the peptide bond cleavage reaction in some enzyme-substrate interactions that is used in the synthesis of new inhibitors. The hydrolytic stability of CÀP bonds is often used in order to prepare stable analogs of bioactive phosphates OÀP(O)(OH) 2 . In addition, aminophosphonic acids and their derivatives are important as metal-complexing agents, which have diagnostic and therapeutic applications, and as industrial chemicals in water treatment, metal extraction, or pollution control.Synthesis, and the chemical, physical, and biological properties of aminophosphonic acids and some directions for their practical application are presented in a number of reviews and book chapters. The most comprehensive account of the chemistry and biology of aminophosphonates and aminophosphinate which covers literature up to 2000 is presented in Kukhar and Hudson ([1] and references therein). Readers are referred to this reference for more detailed information concerning specific aspects of the chemistry and biological activity of aminophosphonic acid derivatives. The purpose of this chapter is to give an updated report on aminophosphonic acids as analogs of amino acids. Numerous heterocyclic compounds that contain both phosphonic and amino groups will not be covered in this report.

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Section: Synthesis Of B-aminophosphonatesmentioning

confidence: 99%

Chemistry of Aminophosphonic Acids and Phosphonopeptides

Kukhar

Romanenko

2009

Amino Acids, Peptides and Proteins in Organic Chemistry

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“…However, even relatively poor information on their complexing power [8,9] and other practically important properties [10] suggests some specificity of their extracting, membrane-transfer, and…”

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confidence: 99%

Synthesis of β-Aminophosphonates and Study of Their Acid-Base Properties and Phase Distribution in Water-Organic Solvent Systems

et al. 2005

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New and previously known -aminoethylphosphonates were synthesized by addition of primary and secondary amines to vinylphosphonates, and their IR and NMR spectra were examined. Diethyl 2-diethylaminoethylphosphonate and diethyl 2-morpholinoethylphosphonate were found to be stronger bases than the corresponding aminomethylphosphonates, but all these are weaker bases than their precursors, nonphosphorylated amines. Distribution constants of -aminophosphonates between water and some organic solvents were determined and compared with those of their -amino homologs.In the series of our preceding publications we described methods of synthesis and acid-base properties of a large number of -aminophosphoryl compounds [1] which can be regarded as phosphorus-containing analogs of natural amino acids. In the recent years, these compounds attract attention of researchers working in the fields of not only fine organic synthesis and chemistry of biologically active substances but also related sciences, such as biochemistry, pharmacology, medicine, agricultural chemistry, etc. [2, 3]. Apart from high efficiency as bioactive substances, -aminophosphoryl compounds were shown to be capable of forming complexes with various species, including metal ions, organic and inorganic acids, etc. [4,5]. In particular, we studied -aminophosphonates as extractants which ensured selective separation of noble metal ions from concomitant elements [6]. Variation of substituents at the phosphorus, -carbon, and nitrogen atoms over a wide range showed that the most selective extractants were those aminophosphoryl reagents which contained more than 20 carbon atoms; in this case, the optimal hydrophilic-lipophilic balance was achieved. It should be emphasized specially that the above information was deduced by analysis of correlations between the number of carbon atoms in the extractant molecules and their distribution constants in waterorganic solvent systems [7]. Therefore, the latter parameter is necessary to elucidate the structure-property relations with a view to effect subsequent purposeful synthesis of extractants, bioactive, and other potentially useful substances possessing an optimal combination of the desired characteristics.The present article opens a series of publications on the synthesis and study of extracting, membranetransfer, and ionophoric properties of a new class of phosphorus-and-nitrogen-containing complexing agents, -aminophosphoryl compounds. Here, we report on the synthesis, acid-base properties, and distribution constants in two-phase aqueous-organic systems of a series of previously described and new -aminophosphonates. When possible, the parameters under study were compared with the data for their analogs, -aminophosphonates, and precursors, the corresponding amines. We believe that such analysis is useful for estimation of factors responsible for physiological and complexing properties of the compounds under study.Properties of -phosphorylated amines have been studied to a considerably lesser extent, as compared to their ...

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ChemInform Abstract: 1,2‐Phosphorylated Aziridines.

Abstract: 2‐Diethoxyphosphorylaziridine (I) is coupled with the phosphorochloridate (II) or the phosphorodiamidic chloride (IV) to give the title compounds (III) and (V) respectively.

Cited by 2 publications

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Chemistry of Aminophosphonic Acids and Phosphonopeptides

Chemistry of Aminophosphonic Acids and Phosphonopeptides

Synthesis of β-Aminophosphonates and Study of Their Acid-Base Properties and Phase Distribution in Water-Organic Solvent Systems

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