General Information

    • DRAMP ID

    • DRAMP29033

    • Peptide Name

    • Stripe-based foldamer peptide 5

    • Sequence

    • KLLKKⓏGKLLKKⓍGKLLKKAG

    • Sequence Length

    • 21

    • Original Sequence

    • KLLKKAGKLLKKAGKLLKKAG

    • Source

    • Synthetic construct

Activity Information

    • Biological Activity

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

    • Comments

    • Function: Antibacterial activity against Gram-positive and Gram-negative bacteria. It is a helical foldmer peptide based on "Stripe" (an AMP manually designed) by introducing a hydrocarbon stapling. The peptide showed weaker activity than Stripe.

    • Target Organism

      • [Ref.33369262] Gram-positive bacteria: Staphylococcus aureus NBRC13276 (MIC = 25 μM) ;
      • Gram-negative bacteria: Escherichia coli DH5α (MIC = 6.25 μM), Pseudomonas aeruginosa NBRC13275 (MIC = 12.5 μM), multidrug-resistant Pseudomonas aeruginosa ATCCBAA-2111 (MDRP) (MIC = 25 μM)

    • Hemolytic Activity

      • [Ref.33369262] It exhibits hemolysis at 1.56 μM agasint human red blood cells.

    • Cytotoxicity

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

Structure Information

    • Linear/Cyclic

    • Cyclic (Stapled)

    • N-terminal Modification

    • Free

    • C-terminal Modification

    • Free

    • Special Amino Acid and Stapling Position

    • ①The Ⓩ (position: 6) in sequence denotes (R)-(7-octenyl)alanine. ②The Ⓧ (position: 13) in sequence denotes (S)-(4-pentenyl)alanine. ③ Ⓩ (6) and Ⓧ (13) are cross-linked by side-stapling through a undec-4-enyl staple.

    • Stereochemistry

    • L

    • Secondary Structure

    • α-Helix content = 34% in 20 mM phosphate buffered saline (PBS) solution (pH 7.4), with 1% sodium dodecyl sulfate

    • Structure Description

    • [Ref.33369262] As shown in Figure 2, peptides 2, 3, 4 and 5 showed negative maxima at around 208 and 222nm, which suggests that they formed stable α-helical structures, similar to Stripe.

    • Helical Wheel Diagram

    • DRAMP29033 helical wheel diagram

    • Predicted Structure

    • There is no predicted structure for DRAMP29033.

Physicochemical Information

    • Formula

    • C₁₁₇H₂₁₉N₃₁O₂₁

    • Absent Amino Acids

    • CDEFHIMNPQRSTVWY

    • Common Amino Acids

    • K

    • Mass

    • 2396.18

    • PI

    • /

    • Basic Residues

    • 9

    • Acidic Residues

    • 0

    • Hydrophobic Residues

    • 7

    • Hydrophobicity

    • /

    • Polar Residues

    • 3

DRAMP29033

Literature Information

  • Literature 1

    • Title

    • Rational Design of Helix-Stabilized Antimicrobial Peptide Foldamers Containing α,α-Disubstituted Amino Acids or Side-Chain Stapling

    • Reference

    • Chempluschem. 2020 Dec;85(12):2731-2736. doi: 10.1002/cplu.202000749.

    • Author

    • Motoharu Hirano, Chihiro Saito, Chihiro Goto, Hidetomo Yokoo, Ryuji Kawano, Takashi Misawa, Yosuke Demizu