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Related Concept Videos

Structure of Amines01:19

Structure of Amines

3.2K
The hybridized nitrogen atom in amines possesses a lone pair of electrons and is bound to three substituents with a bond angle of around 108°, which is less than the tetrahedral angle of 109.5°. However, the C–N–H bond angle is slightly larger at 112°, with a carbon–nitrogen bond length of 147 pm. This carbon–nitrogen bond length of of amines is longer than the carbon–oxygen bond of alcohols (143 pm) but shorter than alkanes’ carbon–carbon bond (154 pm). These aspects are...
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¹H NMR of Conformationally Flexible Molecules: Variable-Temperature NMR01:15

¹H NMR of Conformationally Flexible Molecules: Variable-Temperature NMR

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The axial and equatorial protons in cyclohexane can be distinguished by performing a variable-temperature NMR experiment. In this process, except for one proton, the remaining eleven protons are replaced by deuterium. The deuterium substitution avoids the possible peak splitting caused by the spin-spin coupling between the adjacent protons. The remaining proton flips between the axial and equatorial positions.
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¹H NMR of Conformationally Flexible Molecules: Temporal Resolution00:52

¹H NMR of Conformationally Flexible Molecules: Temporal Resolution

1.2K
At room temperature, the chair conformer of cyclohexane undergoes rapid ring flipping between two equivalent chair conformers at a rate of approximately 105 times per second. These two chair conformers are in equilibrium. The rapid ring flipping results in the interconversion of the axial proton to an equatorial proton and an equatorial to the axial proton. Such interconversions are too rapid and cannot be detected on the NMR timescale. Hence, the NMR spectrometer cannot distinguish between the...
1.2K
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

3.5K
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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Induced-fit Model01:13

Induced-fit Model

88.6K
Most chemical reactions in cells require enzymes—biological catalysts that speed up the reaction without being consumed or permanently changed. They reduce the activation energy needed to convert the reactants into products. Enzymes are proteins, that usually work by binding to a substrate—a reactant molecule that they act upon.
Enzymes exhibit substrate specificity, meaning that they can only bind to certain substrates. This is mainly determined by the shape and chemical...
88.6K
Conformations of Cycloalkanes02:29

Conformations of Cycloalkanes

14.0K
Adolf von Baeyer attempted to explain the instabilities of small and large cycloalkane rings using the concept of angle strain — the strain caused by the deviation of bond angles from the ideal 109.5° tetrahedral value for sp3  hybridized carbons. However, while cyclopropane and cyclobutane are strained, as expected from their highly compressed bond angles, cyclopentane is more strained than predicted, and cyclohexane is virtually strain-free. Hence, Baeyer’s theory that...
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Related Experiment Video

Updated: Jan 11, 2026

Chemical Modification of the Tryptophan Residue in a Recombinant Ca2+-ATPase N-domain for Studying Tryptophan-ANS FRET
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Chemical Modification of the Tryptophan Residue in a Recombinant Ca2+-ATPase N-domain for Studying Tryptophan-ANS FRET

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Conformational Analysis of 3-Indoleacetamide: Unveiling Structural Rigidity in the Tryptophan-Derived Bioactive

Sofía Municio1, Sergio Mato1, José Luis Alonso1

  • 1Grupo de Espectrocopía Molecular (GEM), Edificio Quifima, Laboratorios de Espectroscopia y Bioespectroscopia, Unidad Asociada CSIC, Parque Científico UVa, Universidad de Valladolid, 47011 Valladolid, Spain.

Molecules (Basel, Switzerland)
|November 13, 2025
PubMed
Summary

3-indoleacetamide shows remarkable conformational rigidity, unlike other tryptophan derivatives. This structural constraint offers insights into how molecular shape influences biological functions like plant hormone regulation.

Keywords:
3-indoleacetamideFourier transform microwave spectroscopyplant hormonestructure-propertytryptophan derivatives

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PCR Mutagenesis, Cloning, Expression, Fast Protein Purification Protocols and Crystallization of the Wild Type and Mutant Forms of Tryptophan Synthase
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Investigating Protein Sequence-structure-dynamics Relationships with Bio3D-web
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Last Updated: Jan 11, 2026

Chemical Modification of the Tryptophan Residue in a Recombinant Ca2+-ATPase N-domain for Studying Tryptophan-ANS FRET
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Chemical Modification of the Tryptophan Residue in a Recombinant Ca2+-ATPase N-domain for Studying Tryptophan-ANS FRET

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PCR Mutagenesis, Cloning, Expression, Fast Protein Purification Protocols and Crystallization of the Wild Type and Mutant Forms of Tryptophan Synthase
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Investigating Protein Sequence-structure-dynamics Relationships with Bio3D-web
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Investigating Protein Sequence-structure-dynamics Relationships with Bio3D-web

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Area of Science:

  • Molecular Spectroscopy
  • Biophysical Chemistry
  • Organic Chemistry

Background:

  • 3-indoleacetamide is a crucial intermediate in plant hormone biosynthesis.
  • Tryptophan derivatives exhibit diverse biological roles, including neurotransmission and hormone regulation.
  • Understanding molecular conformation is key to elucidating structure-activity relationships.

Purpose of the Study:

  • To investigate the conformational landscape of 3-indoleacetamide.
  • To compare its conformational rigidity with related tryptophan derivatives.
  • To explore the link between molecular structure and biological function.

Main Methods:

  • Laser-ablation chirped-pulse Fourier transform microwave (LA-CP-FTMW) spectroscopy.
  • Laser-ablation molecular beam Fourier transform microwave (LA-MB-FTMW) spectroscopy.
  • Analysis of rotational transitions (a-, b-, and c-type).

Main Results:

  • 3-indoleacetamide displays unprecedented conformational rigidity.
  • Only a single stable conformer was identified for 3-indoleacetamide.
  • This contrasts with the conformational flexibility of tryptophan, serotonin, tryptamine, and 3-indoleacetic acid.

Conclusions:

  • The acetamide group imposes a unique structural constraint on 3-indoleacetamide.
  • Conformational rigidity may correlate with specific biological functions.
  • Provides new perspectives on structure-activity relationships in bioactive natural products.