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Related Concept Videos

Molecules with Multiple Chiral Centers02:25

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Molecules that possess multiple chiral centers can afford a large number of stereoisomers. For instance, while some molecules like 2-butanol have one chiral center, defined as a tetrahedral carbon atom with four different substituents attached, several molecules like butane-2,3-diol have multiple chiral centers. A simple formula to predict the number of stereoisomers possible for a molecule with n chiral centers is 2n. However, there can be a lower number where some of the stereoisomers are...
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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.
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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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Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen, phosphorus and sulfur centers, including trivalent molecules with lone pairs. Here, the lone pair behaves as a functional group in addition to the other three substituents to form an analogous tetrahedral center that can be chiral.
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The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
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Related Experiment Video

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Synthesis of Compound Giant Unilamellar Vesicles: A Biomimetic Model of Nucleate Cells
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Lysine-based chiral vesicles.

Guihua Li1, Lei Feng1, Peini Zhao1

  • 1Key Laboratory of Colloid and Interface Chemistry, Shandong University, Ministry of Education, Jinan 250100, China.

Journal of Colloid and Interface Science
|July 13, 2014
PubMed
Summary
This summary is machine-generated.

Researchers created chiral vesicles using lysine and DEHPA. Self-assembly is driven by hydrogen bonding and electrostatic interactions, leading to unique chiral properties in the resulting aggregates.

Keywords:
Aggregation behaviorBiological moleculeChiralityHydrogen bondingLysine

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Area of Science:

  • Supramolecular chemistry
  • Materials science
  • Biophysical chemistry

Background:

  • Amino acids like lysine can self-assemble into complex structures.
  • Di-(2-ethylhexyl) phosphoric acid (DEHPA) is a surfactant capable of forming ion pairs.

Purpose of the Study:

  • To investigate the self-assembly of lysine enantiomers with DEHPA in aqueous solutions.
  • To understand the driving forces behind vesicle formation and the role of chirality.

Main Methods:

  • Preparation of uni-lamellar and multi-lamellar vesicles using L-lysine and D-lysine with DEHPA.
  • Analysis of ion-pair formation via acid-base reactions.
  • Investigation of self-assembly mechanisms, including hydrogen bonding and electrostatic interactions.
  • Characterization of microstructural transitions (aggregates, micelles, vesicles).

Main Results:

  • Vesicles were successfully formed from both L-lysine and D-lysine with DEHPA.
  • Self-assembly was driven by hydrogen bonding between lysine side chains and DEHPA polar groups, alongside electrostatic interactions.
  • The combination of these interactions reduced hydrophilic group area, enhancing surface activity and inducing structural transitions.
  • Chirality of lysine led to diverse chiral properties in the self-assembled aggregates.

Conclusions:

  • Lysine enantiomers and DEHPA can form self-assembled vesicles in water.
  • Hydrogen bonding and electrostatic interactions are key drivers for vesicle formation and microstructural transitions.
  • The chirality of lysine imparts unique chiral characteristics to the self-assembled structures.