Amino alcohol based chiral solvating agents: synthesis and applications in the NMR enantiodiscrimination of carboxylic acids

Bozkurt, Selahattin; Durmaz, Mustafa; Naziroglu, Hayriye Nevin; Sirit, Abdulkadir

doi:10.1016/j.tetasy.2011.02.028

Cited by 36 publications

(15 citation statements)

References 51 publications

(10 reference statements)

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“…In nature, serine and threonine (hydroxy amino acids) contain the β‐amino alcohol subunit and this unit is found in many natural products and peptides . The β‐amino alcohol subunit is an important building block for the synthesis of many organic and biomolecules such as unnatural amino acids, chiral ligands and chiral auxiliaries and also as a potential catalyst for the enantioselective reactions . Moreover, it is the key functionality in beta‐blockers and adrenergic drugs.…”

Section: Introductionmentioning

confidence: 99%

Enantiomeric differentiation of β-amino alcohols under electrospray ionization mass spectrometric conditions

et al. 2014

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The enantiomeric differentiation of a series of chiral β-amino alcohols (A) is attempted, for the first time, by applying the kinetic method using L-proline, L-tryptophan, 4-iodo-L-phenylalanine or 3, 5-diiodo-L-tyrosine as the chiral references (Ref) and Cu(2+) or Ni(2+) ion (M) as the central metal ion. The trimeric diastereomeric adduct ions, [M+(Ref)2+A-H](+), formed under electrospray ionization conditions, are subjected for collision-induced dissociation (CID) experiments. The products ions, formed by the loss of either a reference or an analyte, detected in the CID spectra are evaluated for the enantiomeric differentiation. All the references showed enantiomeric differentiation and the R(chiral) values are better for the aromatic alcohols than for aliphatic alcohols. Notably, the R(chiral) values of the aliphatic amino alcohols enhanced when Ni(2+) is used as the central metal ion. The experimental results are well supported by computational studies carried out on the diastereomeric dimeric complexes. The computational data of amino alcohols is correlated with that of amino acids to understand the structural interaction of amino alcohols with reference molecule and central metal ion and their role on the stabilization of the dimeric complexes. Application of flow injection MS/MS method is also demonstrated for the enantiomeric differentiation of the amino alcohols.

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Section: Introductionmentioning

confidence: 99%

Enantiomeric differentiation of β-amino alcohols under electrospray ionization mass spectrometric conditions

et al. 2014

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“…Thus, following the literature procedure, 44 chiral subunits 8-13 were readily prepared by the regioselective ring opening of the (R)-N-(2,3-epoxypropyl)phthalimide with (S)-phenyl ethylamine, (R)-2-phenyl glycinol, (R)-2-amino-1-butanol, (1R, 2S)-cis-1-amino-2-indanol, indoline and dibenzylamine and subsequent cleavage of chiral phthalimides 8-13 with hydrazine hydrate by refluxing in ethanol.…”

Section: Results and Discussion Design And Synthesis Of The New Hostsmentioning

confidence: 99%

Chiral calix[4]arenes bearing amino alcohol functionality as membrane carriers for transport of chiral amino acid methylesters and mandelic acid

2011

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Novel chiral calix[4]arene derivatives bearing amino alcohol moieties at the lower rim have been synthesized from the reaction of p-tert-butylcalix[4]arene diester with various amino alcohols. The transport of amino acid esters (phenylglycine, phenylalanine, and tryptophan methyl esters hydrochloride) and mandelic acid were studied through chloroform bulk liquid membrane system using chiral calix[4]arenes 15-20. All these receptors have been found to act as carriers for transport of aromatic amino acid methylesters and mandelic acid from the aqueous source phase to the aqueous receiving phase. The influence of calixarene and guest structures upon transport through liquid membrane is discussed.

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“…Three of them gained a difference between the signals of both enantiomers of 0.014 ppm, 25 0.045 ppm, 26 and 0.09 ppm 27 , respectively. Differences of 0.006 ppm, 25 0.018 ppm, 29 and 0.039 ppm 26 were reported. 28 Ibuprofen was also tested with four potential CSAs.…”

Section: Introductionmentioning

confidence: 90%

Method for determination of optical purity of 2‐arylpropanoic acids using urea derivatives based on a 1,1′‐binaphthalene skeleton as chiral NMR solvating agents: Advantages and limitations thereof

et al. 2019

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Five optically active urea derivatives (1-5) were used as NMR solvating agents for analysis of the optical purity of different 2-arylpropanoic acids commonly used as nonsteroidal anti-inflammatory drugs. These novel chiral solvating agents were more efficient at discriminating the respective enantiomers of targets than the chiral solvating agents known so far, without the need to add a base for achieving the signal splitting. The advantages and limits of the use of these novel chiral solvating agents were studied.

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Amino alcohol based chiral solvating agents: synthesis and applications in the NMR enantiodiscrimination of carboxylic acids

Cited by 36 publications

References 51 publications

Enantiomeric differentiation of β-amino alcohols under electrospray ionization mass spectrometric conditions

Enantiomeric differentiation of β-amino alcohols under electrospray ionization mass spectrometric conditions

Chiral calix[4]arenes bearing amino alcohol functionality as membrane carriers for transport of chiral amino acid methylesters and mandelic acid

Method for determination of optical purity of 2‐arylpropanoic acids using urea derivatives based on a 1,1′‐binaphthalene skeleton as chiral NMR solvating agents: Advantages and limitations thereof

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