General Information

    • DRAMP ID

    • DRAMP21586

    • Peptide Name

    • 3PR3-X

    • Sequence

    • KⓍWKLⓍKPKⓍWKLⓍK

    • Sequence Length

    • 15

    • Original Sequence

    • /

    • Source

    • Synthetic construct

    • SMILES

    • CC(C)C[C@@H]1NC(=O)[C@H](CCCC[NH3+])NC(=O)[C@H](Cc2c[nH]c3ccccc23)NC(=O)[C@](C)(NC(=O)[C@@H](CCCC[NH3+])NC(=O)[C@H]2CCCN2C(=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](Cc3c[nH]c4ccccc34)C(=O)N[C@@H](CCCC[NH3+])C(=O)N[C@@H](CC(C)C)C(=O)N2)CCCC=CCCC[C@@](C)(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

      • Gram-positive bacteria: Bacillus subtilis ATCC 6633 (MIC = 3.1 μg/mL), Staphylcocccus aureus ATCC 6538p (MIC = 4.7 μg/mL), Staphylcococcus epidermis ATCC 12228 (MIC = 12.5 μg/mL);
      • Gram-negative bacteria: Escherichia coli ATCC 25922 (MIC = 3.1 μg/mL), Shigella dysentariae ATCC 9752 (MIC = 6.3 μg/mL), Salmonella typhimurium ATCC 14028 (MIC = 12.5 μg/mL), Klebsiella pneumonia ATCC 10031 (MIC = 4.7 μg/mL), Pseudomonas aeruginosa ATCC 27853 (MIC = 9.4 μg/mL)

    • Hemolytic Activity

      • It has 5.7% hemolysis against human red blood cells at 6.3 μM and 9.7% hemolysis at 12.5 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, 10 and 14) in sequence indicates (S)-α-methyl, α-pentenylglycine. ②Ⓧ (2) and Ⓧ (6), Ⓧ (10) and Ⓧ (14) are cross-linked respectively by hydrocarbon stapling through an oct-4-enyl hydrocarbon staple.

    • Stereochemistry

    • L

    • Secondary Structure

    • α-helix in a 25 mM potassium phosphate buffer solution at 20 ℃

    • Structure Description

    • Whereas all other dimeric analogs were obtained as a single exclusive product, the proline-containing sequence yielded two products (3PR3-X and 3PR3-Y) in similar amounts. These might be conformational isomers induced by the cis–trans configuration of the proline linker. 3PR3-X, which showed the weakest hemolytic activity, displayed a CD spectrum similar to that of the monomeric S3 and the lowest helical content in this series.
  • There is no predicted structure for DRAMP21586.

Literature Information

  • Literature 1

    • Title

    • Antimicrobial and Hemolytic Activity of Stapled Heptapeptide Dimers

    • Reference

    • B KOREAN CHEM SOC. 2016 Aug;37(8)1199-1203. doi: 10.1002/bkcs.10839.

    • Author

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