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Related Concept Videos

Chirality02:25

Chirality

29.8K
Chirality is a term that describes the lack of mirror symmetry in an object. In other words, chiral objects cannot be superposed on their mirror images. For example, our feet are chiral, as the mirror image of the left foot, the right foot, cannot be superposed on the left foot.
Chiral objects exhibit a sense of handedness when they interact with another chiral object. For example, our left foot can only fit in the left shoe and not in the right shoe. Achiral objects — objects that have...
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Pharmacodynamic Models: Link Model and Systems Pharmacodynamic Model01:14

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The link model is a fundamental pharmacokinetic-pharmacodynamic (PK–PD) approach to account for delayed drug responses when the observed effect does not immediately correlate with the drug's plasma concentration peak. This delay is mathematically addressed by introducing an effect compartment concentration, Ce, which is kinetically linked to the plasma concentration, Cp, via a first-order rate constant, ke0. The linkage allows for a more accurate prediction of drug effects over time. A...
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Chirality in Nature02:30

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Chirality is the most intriguing yet essential facet of nature, governing life’s biochemical processes and precision. It can be observed from a snail shell pattern in a macroscopic world to an amino acid, the minutest building block of life. Most of the snails around the world have right-coiled shells because of the intrinsic chirality in their genes. All the amino acids present in the human body exist in an enantiomerically pure state, except for glycine - the sole achiral amino acid.
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NMR Spectroscopy: Spin–Spin Coupling01:08

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The spin state of an NMR-active nucleus can have a slight effect on its immediate electronic environment. This effect propagates through the intervening bonds and affects the electronic environments of NMR-active nuclei up to three bonds away; occasionally, even farther. This phenomenon is called spin–spin coupling or J-coupling. Coupling interactions are mutual and result in small changes in the absorption frequencies of both nuclei involved. While nuclei of the same element are involved...
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Spin–Spin Coupling: One-Bond Coupling01:17

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Coupling interactions are strongest between NMR-active nuclei bonded to each other, where spin information can be transmitted directly through the pair of bonding electrons. While nuclei polarize their electrons to the opposite spins, the bonding electron pair has opposite spins. Configurations with antiparallel nuclear spins are expected to be lower in energy. When coupling makes antiparallel states more favorable, J is considered to have a positive value. The one-bond coupling constant, 1J,...
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Spin–Spin Coupling Constant: Overview01:08

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In bromoethane, the three methyl protons are coupled to the two methylene protons that are three bonds away. In accordance with the n+1 rule, the signal from the methyl protons is split into three peaks with 1:2:1 relative intensities. The methylene protons appear as a quartet, with the relative intensities of 1:3:3:1.
Qualitatively, any spin plus-half nucleus polarizes the spins of its electrons to the minus-half state. Consequently, the paired electron in the hydrogen–carbon bond must...
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A Micropatterning Assay for Measuring Cell Chirality
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Spin Selectivity in Chiral Linked Systems.

Aleksandra A Ageeva1, Ekaterina A Khramtsova1,2, Ilya M Magin1

  • 1Laboratory of Magnetic Phenomena, Voevodsky Institute of Chemical Kinetics and Combustion SB RAS, Institutskaya 3, 630090, Novosibirsk, Russia.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|January 10, 2018
PubMed
Summary
This summary is machine-generated.

Spin selectivity in electron transfer (ET) was observed in naproxen dyads. Chemically induced dynamic nuclear polarization (CIDNP) revealed differences between (R,S)- and (S,S)-diastereomers, suggesting spin effects influence stereoselectivity.

Keywords:
chiralitydiastereomerselectron transferhydrogen bondsspin selectivity

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Area of Science:

  • Chemical Physics
  • Organic Chemistry
  • Biophysical Chemistry

Background:

  • Stereoselectivity in drug activity of enantiomers remains unexplained.
  • Spin effects are highly sensitive to molecular dynamics and paramagnetic particle interactions.
  • Electron transfer (ET) in molecular dyads offers a platform to study spin-dependent phenomena.

Purpose of the Study:

  • To investigate spin selectivity in electron transfer (ET) of diastereomers.
  • To explore the relationship between spin dynamics and stereoselectivity in molecular dyads.
  • To elucidate the role of spin effects in the observed differences between diastereomers.

Main Methods:

  • Synthesis of (R,S)-naproxen-(S)-N-methylpyrrolidine and (R,S)-naproxen-(S)-tryptophan dyads.
  • Utilizing chemically induced dynamic nuclear polarization (CIDNP) to measure spin selectivity.
  • Comparing experimental CIDNP enhancement coefficients with calculated values.
  • Employing high-resolution X-ray and NMR spectroscopy to study dyad aggregation.

Main Results:

  • Significant spin selectivity in ET was observed for the diastereomers.
  • CIDNP enhancement coefficients for (R,S)-diastereomers were double those of the (S,S)-analogue.
  • Differences in hyperfine interaction constants (HFIs) and paramagnetic lifetimes between diastereomers were confirmed.
  • Concentration-dependent CIDNP effects were observed, attributed to dimer formation.

Conclusions:

  • Spin selectivity in electron transfer is a key factor influencing molecular interactions in naproxen dyads.
  • CIDNP is a sensitive probe for detecting differences in spin and molecular dynamics between diastereomers.
  • Dyad aggregation into dimers can modulate electron transfer efficiency and CIDNP signals, impacting observed stereoselectivity.