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Related Concept Videos

Peptide Bonds02:43

Peptide Bonds

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A peptide bond covalently attaches amino acids through a dehydration reaction. One amino acid's carboxyl group and another amino acid's amino group combine, releasing a water molecule. The resulting bond is the peptide bond. The products that such linkages form are peptides. As more amino acids join this growing chain, the resulting chain is a polypeptide. Each polypeptide has a free amino group at one end. This end has the N-terminal, or the amino-terminal, and the other end has a free...
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Cis-regulatory Sequences02:02

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Cis-regulatory sequences are short fragments of non-coding DNA that are present on the same chromosomes as the genes that they regulate. These fragments serve as binding sites for transcriptional regulators, proteins that are responsible for controlling gene transcription and differential gene expression across cell types in eukaryotes. Cis-regulatory sequences can be close to the gene of interest or thousands of bases away in the DNA sequence; however, those sequences that are further away are...
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Conformity is the change in a person’s behavior to go along with the group, even if that person does not agree with the group.
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Unlike ethane and propane that have only two major conformations, butane has more than two conformers. The staggered form of butane in which the bulky methyl groups on the two carbons are placed on opposite sides, that is, at a dihedral angle of 180°, is the lowest energy, most stable form — called the anti conformer. This conformation is stabilized due to the absence of steric repulsion between the largely spaced out methyl groups. The other two staggered conformations are...
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Stereoisomerism of Cyclic Compounds02:33

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In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
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Constructing Cyclic Peptides Using an On-Tether Sulfonium Center
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Cyanobacterial Cyclic Peptides Containing cis-Pro Conformation.

Jabal Rahmat Haedar1, Abujunaid Habib Khan1, Christopher R Coxon2

  • 1Latvian Institute of Organic Synthesis, Riga, Latvia.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|January 23, 2026
PubMed
Summary
This summary is machine-generated.

Cyanobacterial cyclic peptides often contain proline, influencing their activities. This review highlights the prevalence and characteristics of cis-Pro conformations in these natural products, crucial for understanding their function.

Keywords:
cis‐pro conformationcyanobacteriacyclic peptidesnatural productsprolyl amide bond

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Area of Science:

  • Natural Product Chemistry
  • Biochemistry
  • Structural Biology

Background:

  • Over 3,000 natural products from cyanobacteria exhibit diverse bioactivities, including antiparasitic, anti-inflammatory, antimicrobial, and anticancer properties.
  • Cyanobacterial cyclic peptides, key sources of these natural products, frequently incorporate proline residues, which can exist in cis or trans conformations.
  • The specific proline conformation (cis-Pro) can significantly impact peptide structure, function, and interactions, yet is often underreported in scientific literature.

Purpose of the Study:

  • To review the Nuclear Magnetic Resonance (NMR) characteristics and biosynthetic logic of cyanobacterial cyclic peptides with dominant cis-Pro conformations.
  • To provide a comprehensive overview of cis-Pro conformations within this class of natural products.
  • To elucidate the significance of proline cis/trans isomerism in cyclic peptides.

Main Methods:

  • Manual review of chemical structures and NMR chemical shifts for 150 proline-containing cyanobacterial cyclic peptides.
  • Identification and analysis of peptides with cis-prolyl amide bonds.
  • Explanation of proline cis/trans isomerism and its implications.

Main Results:

  • 51 out of 150 reviewed cyanobacterial cyclic peptides were found to possess cis-prolyl amide bonds.
  • Analysis focused on NMR data to characterize these cis-Pro dominant conformations.
  • The study systematically documented the occurrence of cis-Pro conformations in cyanobacterial cyclic peptides.

Conclusions:

  • Cis-Pro conformations are a significant feature in a notable subset of cyanobacterial cyclic peptides.
  • Understanding proline isomerism is critical for characterizing the bioactivity and function of these natural products.
  • Future research should employ advanced methods to better study and characterize proline cis/trans conformations.