C5241

Sigma

 

Cinnamycin

>95% (HPLC), solid

Synonym:Ro 09-0198
Amino Acid Sequence:Cys-Arg-Gln-Cys-Cys--3-NH2-Ala-Phe-Gly-Pro-Phe-(2S,3S)-2-amino-3-mercaptobutanoyl-Phe-Val-Cys-3-OH-α-Asp-Gly-Asn-(2S,3S)-2-amino-3-mercaptobutanoyl-Lys Disulfide bridges: 1-18, 4-14, 5-11; Lysinoalanine bridge: 6-19
CAS Number:110655-58-8
Linear Formula:C89H125N25O25S3
Molecular Weight:2041.29
MDL number:MFCD01770867

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Description

Biochem/physiol ActionsCinnamycin (Ro 09-0198) is a tetracylic peptide antibiotic (19 amino acids) that binds specifically to the cell surface phosphatidylethanolamine and subsequently induces cytolysis. This is a rare example of a small peptide binding to a particular lipid (1:1 complex). Cinnamycin belongs to the duramycin-type lantibiotics and contains the unusual thioether lanthionine amino acids.
General descriptionUseful tool for monitoring transbilayer movement of PE in membranes, and studying the functional role of PE in cytokinesis, membrane protein folding, and apoptosis.

Properties

assay>95% (HPLC)
formsolid
color white to off-white
solubilityacetonitrile: water (1:1): ≥5 mg/mL
 methanol: water (1:1): ≥5 mg/mL
storage temp.2-8°C

Safety

Personal Protective EquipmentEyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
Safety Statements22-24/25
WGK Germany3
RTECSGE1745000

References

referenceMachiadze, G., et al., Specific binding of Ro 09-0198 (cinnamycin) to phosphatidylethanolamine: a thermodynamic analysis. Biochemistry 41, 1965-1971, (2002)
 Widdick, D. A. et al., Cloning and engineering of the cinnamycin biosynthetic gene cluster from Streptomyces cinnamoneus cinnamoneus DSM 40005 Proc. Natl. Acad. Sci. U. S. A. 100, 4316-4321, (2003)