General Information

    • DRAMP ID

    • DRAMP21598

    • Peptide Name

    • Ac-DS-14W

    • Sequence

    • KⓍAKAⓍKKⓍAKAⓍWK

    • Sequence Length

    • 15

    • Original Sequence

    • KAAKAAKKAAKAAWK

    • Source

    • Synthetic construct

    • SMILES

    • C[C@@H]1NC(=O)[C@H](CCCC[NH3+])NC(=O)[C@H](C)NC(=O)[C@](C)(NC(=O)[C@@H](CCCC[NH3+])NC(=O)[C@@H](CCCC[NH3+])NC(=O)[C@]2(C)CCCC=CCCC[C@@](C)(NC(=O)[C@@H]([NH3+])CCCC[NH3+])C(=O)N[C@@H](C)C(=O)N[C@@H](CCCC[NH3+])C(=O)N[C@@H](C)C(=O)N2)CCCC=CCCC[C@@](C)(C(=O)N[C@H](Cc2c[nH]c3ccccc23)C(=O)N[C@@H](C=O)CCCC[NH3+])NC1=O

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 = 1.6 μM), Staphylococcus aureus ATCC 6538p (MIC = 4.8 μM), Staphylococcus epidermis ATCC 12228 (MIC = 3.1 μM);
      • Gram-negative bacteria: Escherichia coli ATCC 25922 (MIC = 25 μM), Shigella dysentariae ATCC 9752 (MIC = 25 μM), Salmonella typhimurium ATCC 14028 (MIC = 100 μM), Klebsiella pneumonia ATCC 10031 (MIC = 200 μM), Pseudomonas aeruginosa ATCC 27853 (MIC = 100 μM).

    • Hemolytic Activity

      • [Ref.26235946] It has 22.1% hemolysis against human red blood cells at 12.5 μM and 38.8% 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 ,6, 9 and 13) in sequence indicates (S)-α-methyl, α-pentenylglycine. ②Ⓧ (2) and Ⓧ (6), Ⓧ (9) and Ⓧ (13) 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

    • Doubly-stapled Ac-Ds-14W showed the most enhaced helical contents among this series of peptides.
  • There is no predicted structure for DRAMP21598.

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