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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
Summary
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.
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.
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