Chirality in Biology

Bentley, Ronald

doi:10.1002/3527600906.mcb.200200008

Cited by 10 publications

(10 citation statements)

References 62 publications

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“…1,2 For example, biological receptors for taste and smell are sensitive to enantiomers, the two mirrored images of a chiral molecule, and can chemically differentiate them by producing different responses that we interpret as, for instance, drastically different scents. 3,4 This asymmetry is critical in the case of the physiological action of drugs, where in the worse scenario one enantiomer acts as a medicine while the other has detrimental effects. 5,6 Since such critical biological actions can be related with chirality, several spectroscopic techniques have been developed over the years to differentiate enantiomers.…”

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confidence: 99%

Enantiomer-Selective Molecular Sensing Using Racemic Nanoplasmonic Arrays

et al. 2018

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Building blocks of life show well-defined chiral symmetry which has a direct influence on their properties and role in Nature. Chiral molecules are typically characterized by optical techniques such as circular dichroism (CD) where they exhibit signatures in the ultraviolet frequency region. Plasmonic nanostructures have the potential to enhance the sensitivity of chiral detection and translate the molecular chirality to the visible spectral range. Despite recent progress, to date, it remains unclear which properties plasmonic sensors should exhibit to maximize this effect and apply it to reliable enantiomer discrimination. Here, we bring further insight into this complex problem and present a chiral plasmonic sensor composed of a racemic mixture of gammadions with no intrinsic CD, but high optical chirality and electric field enhancements in the near-fields. Owing to its unique set of properties, this configuration enables us to directly differentiate phenylalanine enantiomers in the visible frequency range.

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confidence: 99%

Enantiomer-Selective Molecular Sensing Using Racemic Nanoplasmonic Arrays

et al. 2018

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“…Chiral molecules play a fundamental role in biology. , Especially in pharmaceutical industry, the knowledge of the absolute configuration is crucial, as enantiomers can have different binding affinities for proteins. , Over the past decades, vibrational circular dichroism (VCD) spectroscopy gained popularity as a method to assign absolute stereochemistry, which triggered the development of sophisticated computational and experimental methods. − …”

Section: Introductionmentioning

confidence: 99%

Beyond the Rosenfeld Equation: Computation of Vibrational Circular Dichroism Spectra for Anisotropic Solutions

Sidler

Bleiziffer

Riniker

2019

J. Chem. Theory Comput.

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The difference in absorption of left and right circularly polarized light by chiral molecules can be described by the Rosenfeld equation for isotropic samples. It allows the assignment of the absolute stereochemistry by comparing experimental and computationally derived spectra. Despite the simple form of the Rosenfeld equation, its evaluation in the infrared regime remained challenging, as the contribution from the magnetic dipole operator is zero within the Born− Oppenheimer (BO) approximation. In order to resolve this issue, "beyond BO" theories had to be developed, among which Stephen's magnetic field perturbation (MFP) approach offers a computationally easily accessible form. In this work, optical activity is discussed for cylindrically symmetric solutions, which cannot be described anymore by Rosenfeld's equation due to broken spherical symmetry. Mathematical properties of natural and electric-field induced anisotropies are discussed on the basis of the gauge-independent theoretical framework of Buckingham and Dunn. The issue of achiral noise arising from external field perturbations is considered, and potential remedies are introduced. Natural anisotropic vibrational circular dichroism (VCD) equations are solved numerically by applying the MFP approach within the Hartree−Fock (HF) formalism. Properties of anisotropic VCD spectra are discussed for R-(+)-methyloxirane and (1S,2S)-cyclopropane-1,2-dicarbonitrile. In particular, by using a group theoretical argument, a gauge-independent lower bound for the quadrupole contribution of C 2 -symmetric molecules can be identified, which allows the importance of additional quadrupole terms in anisotropic VCD spectra calculation to be assessed.

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“…5 Moreover, most part of biological processes involving metabolites and enzymes usually show a high degree of specificity toward only one enantiomer. 6 Right and left handed enantiomers can exhibit large differences in their behavior in the living organisms in terms of recognition by receptors, physiological activity, absorption, distribution and clearance, potency, metabolism and toxicology. In this sense, a large percentage of pharmaceutical agents and drugs are optically active and therefore specifically interact through chiral recognition.…”

Section: Introductionmentioning

confidence: 99%

“…[7][8][9] Following the Food and Drug Administration (FDA) statement, while some drug enantiomers present similar pharmacological effect, such as ibuprofen, others might have completely antagonist harmful activities. 6 Hence, the separation of enantiomers is decisive for both, economic and health concerns. [7][8][9][10] Regardless the targeted application, chiral recognition is a necessary condition to ensure the efficiency of the enantiomers' separation.…”

Section: Introductionmentioning

confidence: 99%