Enantiomeric Recognition of Amine Compounds by Chiral Macrocyclic Receptors

Zhang, Xian Xin; Bradshaw, Jerald S.; Izatt, Reed M.

doi:10.1021/cr960144p

Cited by 499 publications

(265 citation statements)

References 277 publications

(869 reference statements)

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“…-Research on chiral, metallated macrocycles has recently gained fast impetus owing to their importance in biological systems, and their utility as novel probes of nucleic acid structure and sites [1] [2]. During the past several years, a variety of achiral macrocyclic structures have been successfully designed and synthesized through a one-pot template process based on coordination or condensation reactions between molecular components [3].…”

mentioning

confidence: 99%

Chiral and Achiral Macrocyclic Copper(II) Complexes: Synthesis, Characterization, and Comparative Binding Studies with Calf-Thymus DNA

Chauhan

Arjmand

2006

C&B

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The new chiral macrocyclic complexes [1,2-bis(1H-benzimidazol-2-yl)-1- (1,8-dihydro-1,3,5,8,10,12-hexaazacyclotetradecane)-2-hydroxyethanolate] copper(II) and -nickel(II) perchlorate, 3 and 4, respectively, were synthesized by the reaction of 1,2-bis(1H-benzimidazol-2-yl)ethane-1,2-diol (L) and (1,8-dihydro-1,3,5,8,10,12-hexaazacyclotetradecane)copper(II) and -nickel(II) diperchlorate complexes, 1 and 2, respectively. All complexes were characterized by various spectroscopic techniques. Molarconductance measurements showed that all of the complexes are ionic in nature. In complexes 3 and 4, the metal center is encapsulated by the ligand L in a pentacoordinated environment. The optical-rotation values ([a] D ) of 3 and 4 at 258 indicate that the complexes are chiral. Absorption-and fluorescencespectral studies, cyclic voltammetry, and viscosity measurements have been carried out to assess the comparative binding of complexes 1 and 3 with calf thymus (CT)-DNA. Analysis of the results suggests that the new chiral complex 3 binds to CT-DNA through a partial intercalation mode that is different from the binding mode of parent achiral complex 1. The complexes 1 and 3 bind to CT-DNA with binding constants K b of 2.7 Â 10 4 and 6.6 Â 10 4 m À 1 , respectively. Circular-dichroism (CD) studies have been further employed to ascertain the binding mode of complex 3, which is consistent with the other spectral studies.

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confidence: 99%

Chiral and Achiral Macrocyclic Copper(II) Complexes: Synthesis, Characterization, and Comparative Binding Studies with Calf-Thymus DNA

Chauhan

Arjmand

2006

C&B

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“…Discriminative interactions and complexations of a chiral host (e.g., extractant) with enantiomers of a chiral guest (racemate that has to be resolved) bearing stereocenter(s) provide an opportunity for the enantiomer recognition and separation. A wide variety of discriminative interactions has been reported, among them anion recognition, [121][122][123] peptide and protein recognition, 124,125 carbohydrate recognition, 126 and recognition of carboxylic acids, 127 amino compounds, 128,129 and neutral molecules. 130 After the addition of a chiral lipophilic host or extractant confined in the organic phase, a host-mediated phase transfer of the substrate occurs.…”

Section: Enantioselective Extractions Enantioselective Liquid-liquid mentioning

confidence: 99%

Principles, Concepts and Strategies of Stereoselective Synthesis

Andrushko

2013

Stereoselective Synthesis of Drugs and Natural Products

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“…The ability of synthetic receptors to function as artificial enzymes or ion channels [1][2][3], to sense biologically important ions [4,5], to improve chromatographic separation [6][7][8][9][10][11][12][13], and to solubilize, stabilize, and transport drugs is being explored [14,15]. The design of synthetic receptors for host-guest systems is challenging, however, because of the many factors requiring adjustment for selective complexation.…”

Section: Introductionmentioning

confidence: 99%

Noncovalent Complexation of Monoamine Neurotransmitters and Related Ammonium Ions by Tetramethoxy Tetraglucosylcalix[4]arene

Torvinen

Kalenius

Sansone

et al. 2011

J. Am. Soc. Mass Spectrom.

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The noncovalent complexation of monoamine neurotransmitters and related ammonium and quaternary ammonium ions by a conformationally flexible tetramethoxy glucosylcalix[4]arene was studied by electrospray ionization Fourier transform ion cyclotron resonance (ESI-FTICR) mass spectrometry. The glucosylcalixarene exhibited highest binding affinity towards serotonin, norepinephrine, epinephrine, and dopamine. Structural properties of the guests, such as the number, location, and type of hydrogen bonding groups, length of the alkyl spacer between the ammonium head-group and the aromatic ring structure, and the degree of nitrogen substitution affected the complexation. Competition experiments and guest-exchange reactions indicated that the hydroxyl groups of guests participate in intermolecular hydrogen bonding with the glucocalixarene.

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Enantiomeric Recognition of Amine Compounds by Chiral Macrocyclic Receptors

Cited by 499 publications

References 277 publications

Chiral and Achiral Macrocyclic Copper(II) Complexes: Synthesis, Characterization, and Comparative Binding Studies with Calf-Thymus DNA

Chiral and Achiral Macrocyclic Copper(II) Complexes: Synthesis, Characterization, and Comparative Binding Studies with Calf-Thymus DNA

Principles, Concepts and Strategies of Stereoselective Synthesis

Noncovalent Complexation of Monoamine Neurotransmitters and Related Ammonium Ions by Tetramethoxy Tetraglucosylcalix[4]arene

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