Peptide name : Baceridin

Source/Organism : Plant-associated rod-shaped, Gram-positive bacteria

Linear/Cyclic : Cyclic

Chirality : Mix

Peptide length: 6

C-terminal modification: Cyclic

N-terminal modification : Not found

Non-natural peptide information: None

Assay type : MTT assay

Assay time : 72h

Activity : Not found

Cell line : HeLa

Cancer type : Not specified

Other activity : Anti-microbial activity

Amino acid composition bar chart :

Molecular mass : 713.9069 Dalton

Aliphatic index : 2.6

Instability index : -30.866

Hydrophobicity (GRAVY) : 2.8667

Isoelectric point : 5.525

Charge (pH 7) : -0.2399

Aromaticity : 0.166

Molar extinction coefficient (cysteine, cystine): (5500, 5500)

Hydrophobic/hydrophilic ratio : infinite

hydrophobic moment : -0.556

Missing amino acid : C,R,H,Q,T,P,M,E,K,S,D,Y,F,N,G

Most occurring amino acid : L

Most occurring amino acid frequency : 2

Least occurring amino acid : W

Least occurring amino acid frequency : 1

Secondary structure fraction (Helix, Turn, Sheet): (0.5, 0, 0.8)

SMILES Notation: CC[C@H](C)[C@H](NC(=O)[C@H](C)NC(=O)[C@@H](N)Cc1c[nH]c2ccccc12)C(=O)N[C@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)O)C(C)C

1 : Niggemann J, et al. Baceridin, a cyclic hexapeptide from an epiphytic bacillus strain, inhibits the proteasome. Chembiochem. 2014; 15:1021-9. doi: 10.1002/cbic.201300778

Paper title : Baceridin, a cyclic hexapeptide from an epiphytic bacillus strain, inhibits the proteasome.

Doi : https://doi.org/10.1002/cbic.201300778

Abstract : A new cyclic hexapeptide, baceridin (1), was isolated from the culture medium of a plant-associated Bacillus strain. The structure of 1 was elucidated by HR-HPLC-MS and 1D and 2D NMR experiments and confirmed by ESI MS/MS sequence analysis of the corresponding linear hexapeptide 2. The absolute configurations of the amino acid residues were determined after derivatization by GC-MS and Marfey's method. The cyclopeptide 1 consists partially of nonribosomal-derived D- and allo-D-configured amino acids. The order of the D- and L-leucine residues within the sequence cyclo(-L-Trp-D-Ala-D-allo-Ile-L-Val-D-Leu-L-Leu-) was assigned by total synthesis of the two possible stereoisomers. Baceridin (1) was tested for antimicrobial and cytotoxic activity and displayed moderate cytotoxicity (1-2 μg mL(-1)) as well as weak activity against Staphylococcus aureus. However, it was identified to be a proteasome inhibitor that inhibits cell cycle progression and induces apoptosis in tumor cells by a p53-independent pathway.