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Related Concept Videos

Chirality02:25

Chirality

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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.
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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Chirality in Nature02:30

Chirality in Nature

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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 at Nitrogen, Phosphorus, and Sulfur02:30

Chirality at Nitrogen, Phosphorus, and Sulfur

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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.
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
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Molecules with Multiple Chiral Centers02:25

Molecules with Multiple Chiral Centers

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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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Globular and Fibrous Proteins02:21

Globular and Fibrous Proteins

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Many proteins can be classified into two distinct subtypes - globular or fibrous. These two types differ in their shapes and solubilities.
Globular proteins are also known as spheroproteins and typically are approximately round in shape. They contain a mix of amino acid types and contain differing sequences in their primary structures. Globular proteins have many different functions, such as enzymes, cellular messengers, and molecular transporters. These roles often require the proteins to be...
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Eukaryotic Transcription Activators02:42

Eukaryotic Transcription Activators

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Transcription activators are proteins that promote the transcription of genes from DNA to RNA. In most cases, these proteins contain two separate domains ‒ a domain that binds to DNA and a domain for activating transcription; however, in some cases, a single domain is responsible for both binding and activation of transcription, as seen in the glucocorticoid receptor and MyoD.
The binding domains are capable of recognizing and interacting with regulatory sequences on the DNA. These...
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Related Experiment Video

Updated: Feb 9, 2026

An Efficient Method for the Synthesis of Peptoids with Mixed Lysine-type/Arginine-type Monomers and Evaluation of Their Anti-leishmanial Activity
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An Efficient Method for the Synthesis of Peptoids with Mixed Lysine-type/Arginine-type Monomers and Evaluation of Their Anti-leishmanial Activity

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Stabilising Peptoid Helices Using Non-Chiral Fluoroalkyl Monomers.

Diana Gimenez1, Juan A Aguilar1, Elizabeth H C Bromley2

  • 1Department of Chemistry, Durham University, South Road, Durham, DH1 3LE, UK.

Angewandte Chemie (International Ed. in English)
|May 31, 2018
PubMed
Summary

Novel fluoroalkyl monomers control peptoid (peptide-like) secondary structure without chirality or charge. This breakthrough enables new applications in biomaterials and chemical biology by influencing amide bond conformation.

Keywords:
NMR spectroscopyfluorinepeptidomimeticspeptoidssecondary structure

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Synthesis and Mass Spectrometry Analysis of Oligo-peptoids
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Synthesis and Mass Spectrometry Analysis of Oligo-peptoids

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Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

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Last Updated: Feb 9, 2026

An Efficient Method for the Synthesis of Peptoids with Mixed Lysine-type/Arginine-type Monomers and Evaluation of Their Anti-leishmanial Activity
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An Efficient Method for the Synthesis of Peptoids with Mixed Lysine-type/Arginine-type Monomers and Evaluation of Their Anti-leishmanial Activity

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Synthesis and Mass Spectrometry Analysis of Oligo-peptoids
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Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
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Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

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Area of Science:

  • Polymer Chemistry
  • Chemical Biology
  • Biomaterials Science

Background:

  • Peptoids offer stability and modular synthesis advantages for chemical biology, medicine, and biomaterials.
  • Controlling peptoid secondary structure is challenging due to their tertiary amide backbone lacking hydrogen-bonding capacity.
  • Existing methods for conformational control using bulky, charged, or chiral monomers limit broader applications.

Purpose of the Study:

  • To investigate non-chiral, neutral fluoroalkyl monomers for controlling peptoid secondary structure.
  • To demonstrate the influence of fluoroalkyl monomers on cis/trans amide bond equilibria.
  • To design peptoid oligomers with stable helical structures using these novel monomers.

Main Methods:

  • Nuclear Magnetic Resonance (NMR) spectroscopy
  • X-ray crystallography
  • Model peptoid systems and linear peptoid oligomers

Main Results:

  • Fluoroalkyl monomers were shown to influence the cis/trans equilibria of peptoid amide bonds.
  • A significant cis-isomer preference was observed, unprecedented without using chirality or charge.
  • Novel fluoroalkyl monomers enabled the design of linear peptoid oligomers with stable helical structures.

Conclusions:

  • Non-chiral, neutral fluoroalkyl monomers are effective for controlling peptoid conformation.
  • This approach overcomes limitations of previous methods, expanding peptoid applications.
  • The developed monomers facilitate the creation of peptoid-based helical structures.