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Baceridin

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

Baceridin, a cyclic hexapeptide isolated from the culture medium of a plant-related bacillus strain, shows moderate cytotoxicity and weak activity against Staphylococcus aureus. In addition, it is a proteasome inhibitor that inhibits cell cycle progression and induces tumor cell apoptosis through a p53-independent pathway.

Category

Functional Peptides

Catalog number

BAT-014835

CAS number

1622872-91-6

Molecular Formula

C37H57N7O6

Molecular Weight

695.89

Specification
Reference Reading

IUPAC Name

(6S,9R,12S,15S,18R)-3-[(2S)-butan-2-yl]-15-(1H-indol-3-ylmethyl)-18-methyl-9,12-bis(2-methylpropyl)-6-propan-2-yl-1,4,7,10,13,16-hexazacyclooctadecane-2,5,8,11,14,17-hexone

Synonyms

Cyclo(D-alanyl-L-tryptophyl-L-leucyl-D-leucyl-L-valylisoleucyl); Cyclo(-D-Ala-D-allo-Ile-Val-D-Leu-Leu-Trp); cyclo[D-alanyl-L-tryptophyl-L-leucyl-D-leucyl-L-valyl-(3S)-DL-isoleucyl]

Appearance

White Powder

Purity

≥95%

Density

1.1±0.1 g/cm3

Boiling Point

1060.2±65.0°C at 760 mmHg

Sequence

cyclo[D-Ala-Trp-Leu-D-Leu-Val-DL-Ile]

Storage

Store at -20°C

Solubility

Soluble in DMF, DMSO

InChI

InChI=1S/C37H57N7O6/c1-10-22(8)31-37(50)39-23(9)32(45)40-29(17-24-18-38-26-14-12-11-13-25(24)26)34(47)41-27(15-19(2)3)33(46)42-28(16-20(4)5)35(48)43-30(21(6)7)36(49)44-31/h11-14,18-23,27-31,38H,10,15-17H2,1-9H3,(H,39,50)(H,40,45)(H,41,47)(H,42,46)(H,43,48)(H,44,49)/t22-,23+,27-,28+,29-,30-,31?/m0/s1

InChI Key

KULVZQUHMGDNPX-FNDSQMSDSA-N

Canonical SMILES

CCC(C)C1C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N1)C(C)C)CC(C)C)CC(C)C)CC2=CNC3=CC=CC=C32)C

1. Gene gains paved the path to land

Jan de Vries, Stefan A Rensing Nat Plants. 2020 Jan;6(1):7-8. doi: 10.1038/s41477-019-0579-5.

Two genomes of the closest algal sisters to land plants were sequenced, providing potential evidence that bacterial genes were key in adapting to terrestrial stresses.

2. Baceridin, a cyclic hexapeptide from an epiphytic bacillus strain, inhibits the proteasome

Jutta Niggemann, et al. Chembiochem. 2014 May 5;15(7):1021-9. doi: 10.1002/cbic.201300778. Epub 2014 Apr 1.

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.