General Information

    • DRAMP ID

    • DRAMP21565

    • Peptide Name

    • RRR

    • Sequence

    • RⓍWRJⓍR

    • Sequence Length

    • 7

    • Original Sequence

    • /

    • Source

    • Synthetic construct

Activity Information

    • Biological Activity

    • Antimicrobial, Antibacterial, Anti-Gram+, Anti-Gram-

    • Comments

    • Function: Antibacterial activity against Gram-positive and Gram-negative bacteria.

    • Target Organism

      • [Ref.30361948] Gram-positive bacteria: Bacillus subtilis ATCC 6633 (MIC = 12.5 μM), Staphyolococcus aureus ATCC 6538p (MIC = 6.3 μM), Staphylococcus epidermidis ATCC 12228 (MIC = 25 μM);
      • Gram-negative bacteria: Escherichia coli ATCC 25922 (MIC = 25 μM), Shigella dysenteriae ATCC 9752 (MIC = 50 μM), Salmonella typhimurium ATCC 14028 (MIC = 100 μM), Klebsiella pneumoniae ATCC 10031 (MIC = 50 μM), Pseudomonas aeruginosa ATCC 27853 (MIC = 100 μM)

    • Hemolytic Activity

      • [Ref.30361948] It has <1% hemolysis against human red blood cells at 25 μM and 3.2% hemolysis at 50 μM.

    • Cytotoxicity

    • No cytotoxicity information found in the reference(s) presented

Structure Information

    • Linear/Cyclic

    • Cyclic (Stapled)

    • N-terminal Modification

    • Free

    • C-terminal Modification

    • Amidation

    • Special Amino Acid and Stapling Position

    • ①The J (position: 5) in sequence is norleucine. ②The Ⓧ (position: 2 and 6) indicates (S)-α-methyl, α-pentenylglycine. ③Ⓧ (2) and Ⓧ (6) are cross-linked by hydrocarbon stapling through an oct-4-enyl hydrocarbon staple.

    • Stereochemistry

    • L

    • Secondary Structure

    • α-helix in a 25 mM potassium phosphate solution (pH 6.5).

    • Structure Description

    • All analogs displayed similar CD spectra to that of KKK, having two minima near 208 and 222 nm and a maximum near 190nm, which are characteristic of α-helices.

    • Helical Wheel Diagram

    • DRAMP21565 helical wheel diagram

    • Predicted Structure

Literature Information

  • Literature 1

    • Title

    • Effects of lysine-to-arginine substitution on antimicrobial activity of cationic stapled heptapeptides

    • Reference

    • Arch Pharm Res. 2018 Nov;41(11):1092-1097. doi: 10.1007/s12272-018-1084-5. Epub 2018 Oct 25.

    • Author

    • Huy X Luong, Do-Hee Kim, Bong-Jin Lee, Young-Woo Kim