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NMR Spectroscopy of Aromatic Compounds01:14

NMR Spectroscopy of Aromatic Compounds

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Aromatic compounds can be identified or analyzed using proton NMR and carbon‐13 NMR. Typically, aromatic hydrogens or hydrogens directly bonded to the aromatic rings are strongly deshielded by the aromatic ring current. Therefore, they absorb in the range of 6.5–8.0 ppm in proton NMR spectra. For instance, aromatic hydrogens directly bonded to the benzene ring absorb at 7.3 ppm. However, aromatic hydrogens of larger rings absorb farther upfield or downfield than the ideal range.
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Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

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Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous...
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Amino acids03:42

Amino acids

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Amino acids are the monomers that comprise proteins. Each amino acid has the same fundamental structure, which consists of a central carbon atom, or the alpha (α) carbon, bonded to an amino group (NH2), a carboxyl group (COOH), and to a hydrogen atom. Every amino acid also has another atom or group of atoms bonded to the central atom known as the R group. There are 20 common amino acids present in proteins, each with a different R group. Variation in the amino acid sequence is responsible for...
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Noncovalent Attractions in Biomolecules02:35

Noncovalent Attractions in Biomolecules

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Noncovalent attractions are associations within and between molecules that influence the shape and structural stability of complexes. These interactions differ from covalent bonding in that they do not involve sharing of electrons.
Four types of noncovalent interactions are hydrogen bonds, van der Waals forces, ionic bonds, and hydrophobic interactions.
Hydrogen bonding results from the electrostatic attraction of a hydrogen atom covalently bonded to a strong-electronegative atom like oxygen,...
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Noncovalent Attractions in Biomolecules02:35

Noncovalent Attractions in Biomolecules

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Aromatic Compounds: Overview01:25

Aromatic Compounds: Overview

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In general, the term ‘aromatic’ indicates a pleasant smell or fragrance from fresh flowers, freshly prepared coffee, etc. In the early history of organic chemistry, many benzene derivatives were isolated from the pleasant odor oils of the plants. For example, vanillin was isolated from the oil of vanilla, methyl salicylate from the oil of wintergreen, and cinnamaldehyde from the oil of cinnamon. They all had a pleasant odor; hence the name aromatic was given.
In 1825, Faraday isolated...
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Author Spotlight: Unveiling the Structural and Dynamic Aspects of Glycan Molecular Recognition
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Carbohydrate-Aromatic Interactions in Proteins.

Kieran L Hudson1, Gail J Bartlett1, Roger C Diehl2

  • 1School of Chemistry, University of Bristol , Bristol BS8 1TS, United Kingdom.

Journal of the American Chemical Society
|November 13, 2015
PubMed
Summary
This summary is machine-generated.

Aromatic residues like tryptophan are key for protein-carbohydrate interactions. Electronic and electrostatic complementarity drives these essential biological binding events.

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Area of Science:

  • Biochemistry
  • Structural Biology
  • Molecular Interactions

Background:

  • Protein-carbohydrate interactions are crucial in biological processes, yet the fundamental forces governing them remain incompletely understood.
  • Defining and manipulating these interactions is vital for understanding health and disease.

Purpose of the Study:

  • To quantitatively analyze X-ray crystal structures of proteins with bound carbohydrates to identify common features in carbohydrate recognition.
  • To elucidate the role of amino acid side chains, particularly aromatic residues, in protein-carbohydrate complexation.

Main Methods:

  • Quantitative analysis of X-ray crystal structures of protein-carbohydrate complexes.
  • Nuclear Magnetic Resonance (NMR) spectroscopy to study carbohydrate-aromatic interactions in solution.
  • Linear free energy relationship analysis to support electronic effects.

Main Results:

  • Aromatic amino acid side chains, especially tryptophan, are enriched in carbohydrate-binding pockets.
  • Specific carbohydrate C-H bonds preferentially interact with aromatic residues, driven by electronic complementarity.
  • NMR data confirms favorable binding between indole and electron-poor C-H bonds in carbohydrates, highlighting electrostatic contributions.

Conclusions:

  • Electrostatic and electronic complementarity between carbohydrates and aromatic residues are critical drivers of protein-carbohydrate complexation.
  • These weak noncovalent interactions dictate the specificity and positioning of saccharides within protein-binding sites.