Synthesis of phosphonic analogues of carnitine and γ-amino-β-hydroxybutyric acid

Tadeusiak, Elżbieta

doi:10.1016/j.bioorg.2004.05.009

Cited by 6 publications

(6 citation statements)

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“…The special interest in g-aminophosphonic acids is driven by three biomedical research areas: g-aminobutyric acid (GABA) and carnitine phosphonic analogs [205], amino bisphosphonates, and fosmidomycin derivatives. The diversity of structural requirements for these compounds demands special strategies and methods to build the needed molecules.…”

Section: Synthesis Of G-aminophosphonates and Higher Homologs J219mentioning

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 G-aminophosphonates and Higher Homologs J219mentioning

confidence: 99%

Chemistry of Aminophosphonic Acids and Phosphonopeptides

Kukhar

Romanenko

2009

Amino Acids, Peptides and Proteins in Organic Chemistry

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“…It is used in numerous illness treatments including epilepsy therapy (De Maio and Pasquariello, 1963 ; Banfi et al, 1983 ; García-Flores and Farías, 1997 ; Melis et al, 2014 ). Among several GABA and GABOB analogs the γ-amino-β-hydroxy phosphonic acid (P-GABOB) and its organophosphorus derivatives constitute an interesting group of compounds (Dingwall, 1983 ; Yuan et al, 2002 ; Ordóñez et al, 2003 , 2010 ; Wang et al, 2003 ; Wróblewski and Hałajewska-Wosik, 2003 ; Tadeusiak, 2004 ; Figure 2 ).…”

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confidence: 99%

Highly Diastereoselective Construction of Carbon– Heteroatom Quaternary Stereogenic Centers in the Synthesis of Analogs of Bioactive Compounds: From Monofluorinated Epoxyalkylphosphonates to α-Fluoro-, β-, or γ-Amino Alcohol Derivatives of Alkylphosphonates

et al. 2021

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The synthesis of the stable surrogates of an important amino acid (R)-4-amino-3-hydroxybutyric acid (GABOB) such as substituted hydroxy aminophosphonic acids bearing a quaternary stereogenic center is presented. Highly diastereoselective formations of fluorinated spiroepoxy alkylphosphonate or related tertiary carbon-containing oxiranes from β-keto phosphonates possessing methyl, phenyl, or cyclohexenyl substituents, are reported. Stereoselective acid-promoted epoxide opening by bromide or azide followed by reduction/protection afforded tertiary bromides or N-Boc derivatives of β-amino-γ-hydroxy alkylphosphonates in most cases, while the reactions of oxiranes with different amines yielded their β-hydroxy-γ-amino regioisomers. Surprisingly, during the synthesis of amino phosphonic acids, we observe that the acid-induced rearrangement proceeded in a high diastereospecific manner, leading finally to substituted β-hydroxy-γ-aminoalkylphosphonic acids.

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“…[18][19][20][21][22][23][24][25][26][27][28][29][30] In order to check the general reactivity of cyclic phosphates, the cyclic phosphates (14,15) derived from D Derythritol were synthesized, in turn, from the less expensive D D-glucose using a similar protocol as for the synthesis of the corresponding cyclic sulfate (Scheme 2). 20 The diol (16) O six steps using a procedure developed by Satoh et al 31 Various conditions were tried to couple the D D-cyclic phosphates (14, 15) with either compound 17 or tetrahydrothiophene, but the reactions did not proceed as planned (Table 1). However, the reaction did proceed with thiourea as a nucleophile.…”

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“…15 The involvement of carnitine (5) and c-amino-bhydroxybutyric acid (6) in the biology of mammalian cells and some important aspects of medicinal treatment has led to the development of their pharmacologically potent phosphate analogues (7,8). 16 The purinetrione bearing an alkyl phosphate (9) was tested and found to be an inhibitor of lumazine synthase. 17 The structural modification of known inhibitors represents a promising approach in the search for new glycosidase inhibitors.…”

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