Enzymes in organic chemistry. Part 10:  Chemo-enzymatic synthesis of l-phosphaserine and l-phosphaisoserine and enantioseparation of amino-hydroxyethylphosphonic acids by non-aqueous capillary electrophoresis with quinine carbamate as chiral ion pair agent

Hammerschmidt, Friedrich; Lindner, Wolfgang; Wuggenig, Frank; Zarbl, Elfriede

doi:10.1016/s0957-4166(00)00261-5

Cited by 46 publications

(22 citation statements)

References 15 publications

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“…Since CE offers higher efficiency and is therefore supposed to provide higher peak capacity, we tested a previously proposed non aqueous CE method [5,14,19] employing O-(tert-butylcarbamoyl) quinine (Fig. 2a) as chiral additive to a non aqueous background electrolyte for its capability to separate all components of interest in a single run.…”

Section: Stereoselective Ce Methods Applying the Pftmentioning

confidence: 99%

“…Usually, activity is observed only for one enantiomer and, therefore, usability strictly relies on the enantiomeric purity of these chiral compounds. Several concepts for the preparation of such chiral chemical entities with high enantiomeric exess (ee) have been reported to date [2][3][4][5]. In contrast, there are only a few enantioselective analytical methods currently available for chiral phosphonic acids, which might be useful for the study of stereochemical pathways of stereselective reactions and for the determination of the stereochemical purity of the final products.…”

Section: Introductionmentioning

confidence: 99%

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Simultaneous separation of the stereoisomers of 1-amino-2-hydroxy and 2-amino-1-hydroxypropane phosphonic acids by stereoselective capillary electrophoresis employing a quinine carbamate type chiral selector

et al. 2001

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A stereoselective nonaqueous capillary electrophoresis (CE) method utilizing O-(tert-butylcarbamoyl) quinine as chiral ion-pair agent and additive to the non aqueous background electrolyte was evaluated for the simultaneous separation of the enantiomers and diastereomers of 1 -amino-2-hydroxypropane phosphonic acid besides the corresponding beta-aminophosphonic acid analogs, the stereoisomers of 2-amino-1-hydroxypropane phosphonic acid, in a single run. The separations have been carried out using the partial filling technique to avoid strong background signal from the quinine selector. It conveniently allowed the baseline separation of all eight components of interest (alpha- as well as beta-aminophosphonic acids) as N-2,4-dinitrophenyl derivatives in a single run. Moreover, the absolute configurations of all eight peaks were identified. Compared to the quinine carbamate selector, the corresponding 'pseudo-enantiomeric' O-(tert-butylcarbamoyl) quinidine selector exhibited reserved elution order and nearly identical resolutions. The proposed CE method turned out to be advantageous over stereoselective high-performance liquid chromatography (HPLC) with a quinine carbamate type stationary phase, which showed high enantioselectivity, but failed to simultaneously separate all eight components.

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Section: Stereoselective Ce Methods Applying the Pftmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Simultaneous separation of the stereoisomers of 1-amino-2-hydroxy and 2-amino-1-hydroxypropane phosphonic acids by stereoselective capillary electrophoresis employing a quinine carbamate type chiral selector

et al. 2001

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“…Hammerschmidt et al [98] reported on the conversion of the diisopropyl (S)-2-azido-1-hydroxyethylphosphonate (116) into L-phosphaserine (119) via p-nitrobenzenesulfonate 117 (Scheme 43).…”

Section: Nucleophilic Substitution Of -Halogeno Derivatives With Azidesmentioning

confidence: 99%

Synthesis and Reactivity of Azidoalkylphosphonates, -Phosphinates and -Phosphine Oxides

Gajda

2007

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This review will focus on the synthesis of -and -azidoalkylphosphonic and -phosphinic acids, -phosphine oxides and their derivatives as well as their reactions utilizing the azido group and/or phosphyl group. In the first part of this review synthetic routes to such azides will be reviewed. Generally, these compounds are achieved via nucleophilic substitution of hydroxy derivatives of phosphonates, -phosphinates, and -phosphine oxides by the Mitsunobu protocol or by the displacement of their sulfonates or halogen derivatives with azides. The ring-opening of phosphorus-containing oxiranes or cyclic vicinal sulfates with azides will also be discussed. Electrophilic azidation of the corresponding phosphorus-stabilized carbanions has also been described. In the second part of the review emphasis will be placed on the application of azido derivatives in organic synthesis. 1,3-Dipolar cycloaddition is an excellent tool in the construction of fivemembered heterocycles. Therefore, the formation of 1,2,3-triazoles from alkynes, enamines and 2-oxoalkylidenetriphenylphosphoranes will be discussed. Hence, the azido group is easily converted into amine, and phosphorus-containing azides can be considered to be azide-masked equivalents of amino derivatives or their N-protected derivatives. The application of such azides in the synthesis of phosphorus analogs of amino acids will be discussed. The synthesis of carbodiimides, imines, isothiocyanates and phosphonodipeptides has also been reviewed.

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“…Regioselective opening of the aziridine ( R )- 286 with TFA followed by acidic hydrolysis with hydrochloric acid and subsequent ion exchange, afforded the ( R )-phosphoserine 287 in 59% yield (Scheme 76). 167…”

Section: Stereoselective Synthesis Of α-Aminophosphonic Acids and mentioning

confidence: 99%

An overview of stereoselective synthesis of α-aminophosphonic acids and derivatives

2009

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An overview of all methodologies published during the last few years focused to the stereoselective (diastereoselective or enantioselective) synthesis of α-aminophosphonic acids and derivatives is reported. The procedures have been classified according a retrosynthetic strategy and taking into account the formation of each one of the bonds connected to the chiral centre. Keywordsα-Aminophosphonic acids; α-Aminophosphonates; Stereoselective Synthesis; Resolution; Chiral Pool Introducciónα-Aminoalkylphosphonic acids 1 are structurally analogous to α-amino acids 2, obtained by isosteric substitution of planar and less bulky carboxylic acid (CO 2 H) by a tetrahedral phosphonic acid functionality (PO 3 H 2 ). Several aminophosphonic, aminophosphinic and aminophosphonous acids have been isolated from various natural sources either as free amino acids or as constituents of more complex molecules. 1 Many natural and synthetic aminophosphonic acids, their phosphonate esters and short peptides incorporating this unit, exhibit a variety of biological properties. 2 Their diverse applications include enzyme inhibitors 3 such as synthase, 4 HIV protease, 5 rennin, 6 phosphatasa activity, 7 PTPases, 8 and potent antibiotics, 9 as antibacterial agents, 10 antiviral, 11 antifungal, 12 herbicides, 13 antitumor agents. 14 Their role for antibody generation is also well documented. 15 In addition, the incorporation of cyclic amino acids of medium ring size into key positions in peptide chains plays an important role, and constitutes the most prominent pathway to conformationally constrained peptidomimetics, a tool in modern drug discovery. NIH-PA Author ManuscriptNIH-PA Author Manuscript NIH-PA Author ManuscriptIn addition, α-aminophosphonic acids and their monoalkyl esters are also of interest in hydrometallurgy in order to extract metals 17 and in diagnostic medicine as screening agents, once complexed with lanthanides and actinides. 18,19 It is well known that the biological activity of α-aminophosphonic acids and derivatives depends on the absolute configuration of the stereogenic α carbon to phosphorous. 20 For example, (R)-phospholeucine 3 is a more potent inhibitor of leucine aminopeptidase than the S enantiomer, 21 and (S,R)-alafosfalin 4 shows higher antibacterial activity against both Grampositive and Gram-negative microorganisms than the other three diastereoisomers. 22 In view of the different biological and chemical applications of the α-aminophosphonic acids and derivatives, in the last 35 years the development of suitable synthetic methodologies for their preparation in optically pure form has been a topic of great interest in several research groups. In this context, several protocols for efficient asymmetric synthesis of α-aminophosphonic acids and derivatives have emerged in the recent years and several reviews have been published. 23 Now we would like to report herein an update over stereoselective synthesis of α-aminophosphonic acids and derivatives from 1998-2007. The principal synthetic stra...

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Enzymes in organic chemistry. Part 10: Chemo-enzymatic synthesis of l-phosphaserine and l-phosphaisoserine and enantioseparation of amino-hydroxyethylphosphonic acids by non-aqueous capillary electrophoresis with quinine carbamate as chiral ion pair agent

Cited by 46 publications

References 15 publications

Simultaneous separation of the stereoisomers of 1-amino-2-hydroxy and 2-amino-1-hydroxypropane phosphonic acids by stereoselective capillary electrophoresis employing a quinine carbamate type chiral selector

Simultaneous separation of the stereoisomers of 1-amino-2-hydroxy and 2-amino-1-hydroxypropane phosphonic acids by stereoselective capillary electrophoresis employing a quinine carbamate type chiral selector

Synthesis and Reactivity of Azidoalkylphosphonates, -Phosphinates and -Phosphine Oxides

An overview of stereoselective synthesis of α-aminophosphonic acids and derivatives

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