Cavity Effects on the Enantioselectivity of Chiral Amido[4]resorcinarene Stereoisomers

Botta, Bruno; Subissati, Deborah; Tafi, Andrea; Monache, Giuliano Delle; Filippi, Antonello; Speranza, Maurizio

doi:10.1002/ange.200460663

Cited by 12 publications

(21 citation statements)

References 16 publications

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“…The reaction plots of the enantiomeric ␤-amino acids show bimodal behavior showing the existence of fast (k fast ) and slow (k slow ) reacting complexes. The reason for this kind of behavior might be due to possibility that more than one ion population is present and/or there are some "hot" segments in ion population, which are reacting quickly away [34,42]. This same kind of behavior was also observed in our earlier studies of differentiation of diastereomeric ␤-amino acids, for example cyclopentane and cyclohexane ␤-amino acids, when host-guest complexes and ion/ molecule reactions were utilized [38,43].…”

Section: Differentiation Of Enantiomeric 2-aminocyclohexanecarboxylicsupporting

confidence: 66%

Chiral differentiation of some cyclopentane and cyclohexane β-amino acid enantiomers through ion/molecule reactions

Hyyryläinen

Pakarinen

Forró

et al. 2009

J. Am. Soc. Mass Spectrom.

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Section: Differentiation Of Enantiomeric 2-aminocyclohexanecarboxylicsupporting

confidence: 66%

Chiral differentiation of some cyclopentane and cyclohexane β-amino acid enantiomers through ion/molecule reactions

Hyyryläinen

Pakarinen

Forró

et al. 2009

J. Am. Soc. Mass Spectrom.

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“…Speranza applied ESI-MS n CID and REMPI-TOF methodologies to measure the fragmentation thresholds of diastereomeric clusters [19,23,25,32,48,49]. They found that the chiral recognition was very sensitive to cavity size and hydrophilic/hydrophobic properties of the chiral receptor [24,50]. The same group also used gas-phase guest exchange reactions between diastereomeric adducts and chiral or achiral reactants [27,[51][52][53].…”

mentioning

confidence: 99%

Structural relationships in small molecule interactions governing gas-phase enantioselectivity and zwitterionic formation

Cong

Czerwieniec

McJimpsey

et al. 2006

J. Am. Soc. Mass Spectrom.

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Gas-phase zwitterionic amino acids were formed in complexes of underivatized ␤-cyclodextrin through reactions with a neutral base, n-propylamine. The reaction was performed in the analyzer cell of an electrospray ionization-Fourier transform mass spectrometer. Most of the natural amino acids were studied with three cyclodextrin hosts including ␣-, ␤-, and ␥-cyclodextrin to understand better the structural features that lead to the stabilization of the zwitterionic complexes. Molecular dynamics calculations were performed to provide insight into the structural features of the complexes. The rate constants of the reactions were obtained through kinetic plots. Examination of both L-and D-enantiomers of the amino acid showed that the reaction was enantioselective. The reaction was then employed to analyze mixtures of Glu enantiomers naturally occurring in the bacteria Bacillus licheniformis. (J Am Soc Mass Spectrom 2006, 17, 442-452)

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“…With the aim to outline a comprehensive study of the tetramide/nucleosides interaction, we performed a complete [12][13][14][15][16][17] [18].…”

Section: Esi-ft-icr Experimentsmentioning

confidence: 99%

Enantioselective Supramolecular Carriers for Nucleoside Drugs. A Thermodynamic and Kinetic Gas Phase Investigation

Fraschetti

Filippi

Crestoni

et al. 2012

J. Am. Soc. Mass Spectrom.

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The enantioselective interactions between chiral tetra-amidic receptors and is not. The most encouraging result concerning the measured fragmentation and kinetic differences between C and ara-C, that are just epimers, indicates the possibility to subtly modulate the non-covalent drug/receptor interactions, through the electronic properties of the 2'-substituent on the nucleoside furanose ring, and furthermore on its three-dimensional position.

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Cavity Effects on the Enantioselectivity of Chiral Amido[4]resorcinarene Stereoisomers

Cited by 12 publications

References 16 publications

Chiral differentiation of some cyclopentane and cyclohexane β-amino acid enantiomers through ion/molecule reactions

Chiral differentiation of some cyclopentane and cyclohexane β-amino acid enantiomers through ion/molecule reactions

Structural relationships in small molecule interactions governing gas-phase enantioselectivity and zwitterionic formation

Enantioselective Supramolecular Carriers for Nucleoside Drugs. A Thermodynamic and Kinetic Gas Phase Investigation

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