General Information

    • DRAMP ID

    • DRAMP21597

    • Peptide Name

    • Ac-SS-14W

    • Sequence

    • KⓍAKAⓍKKAAKAAWK

    • Sequence Length

    • 15

    • Original Sequence

    • KAAKAAKKAAKAAWK

    • 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.26235946] Gram-positive bacteria: Bacillus subtilis ATCC 6633 (MIC = 25 μM), Staphylococcus aureus ATCC 6538p (MIC = 9.4 μM), Staphylococcus epidermis ATCC 12228 (MIC = 75 μM);
      • Gram-negative bacteria: Escherichia coli ATCC 25922 (MIC = 3.1 μM), Shigella dysentariae ATCC 9752 (MIC = 18.8 μM), Salmonella typhimurium ATCC 14028 (MIC > 200 μM), Klebsiella pneumonia ATCC 10031 (MIC = 18.8 μM), Pseudomonas aeruginosa ATCC 27853 (MIC = 100 μM).

    • Hemolytic Activity

      • [Ref.26235946] It has <1% hemolysis against human red blood cells at 12.5 μM and <1% hemolysis at 25 μM.

    • Cytotoxicity

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

Structure Information

    • Linear/Cyclic

    • Cyclic (Stapled)

    • N-terminal Modification

    • Acetylation

    • C-terminal Modification

    • Amidation

    • Special Amino Acid and Stapling Position

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

    • Stereochemistry

    • L

    • Secondary Structure

    • α-helix in 25 mM potassium phosphate buffer solution (pH6.5)

    • Structure Description

    • On the other hand, singly-stapled analog Ac-SS-14W exhibited a typical CD spectrum for α-helix, characterized by two minima near 208 and 222 nm and a maximum near 190 nm.

    • Helical Wheel Diagram

    • DRAMP21597 helical wheel diagram

    • Predicted Structure

Literature Information

  • Literature 1

    • Title

    • Antimicrobial activity of doubly-stapled alanine/lysine-based peptides

    • Reference

    • Bioorg Med Chem Lett. 2015 Sep 15;25(18):4016-9. doi: 10.1016/j.bmcl.2015.06.053. Epub 2015 Jun 19.

    • Author

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