Cinnamycin from Streptomyces cinnamoneus, ≥95% (HPLC)

Properties

Related Categories	Antibiotics, Antibiotics A to Z, Antibiotics A-F, Antifungal, Bioactive Small Molecules, CI-CY, Cell Biology, Cell Signaling and Neuroscience, Chemical Structure Class, Interferes with Cell Membrane Permeability (Ionophores), Lipids in Cell Signaling, Mechanism of Action, Peptides, Phospholipase Inhibitors, Phospholipid Metabolism, Spectrum of Activity More...
biological source	from Streptomyces cinnamoneus
assay	≥95% (HPLC)
form	solid
solubility	DMSO: soluble10 mg/mL
	acetonitrile: water (1:1): soluble5 mg/mL (requires heating)
storage temp.	2-8°C

Description

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

Biochem/physiol Actions

Cinnamycin is a tetracyclic polypeptide antibiotic containing 19 amino acids. The polypeptide has the unusual amino acids threo-3-methyl-lanthionine, meso-lanthionine, lysinoalanine and 3-hydroxyaspartic acid. It is produced by Streptomyces cinnamoneus and belongs to the duramycin-type l antibiotics. Lantibiotics are synthesized in the ribosome and undergo extensive post-translational modifications to attain their active antimicrobial form.^1,^2,³ The unique receptor for Cinnamycin, phosphatidylethanolamine (PE), is located on the inner leaflet of the plasma membrane.^4,⁵ Cinnamycin induces transbilayer lipid movement leading to the exposure of PE to the outer leaflet of the plasma membrane.^2,^4, The interaction of Cinnamycin with PE provides a tool for PE monitoring.⁵ Cinnamycin is active against Gram-positive rods such as Bacilli, Clostyridium and Mycobacterium, causing cell wall biosynthesis stress.²
Cinnamycin, like other lantibiotics, was also reported to inhibit phospholipase A2 (PLA2).¹ It was suggested as an alternative treatment for atherosclerosis through its ability to inhibit PLA2 by binding to its substrate PE.^2,⁵ Moreover, Cinnamycin was found to inhibit Herpes simplex virus (HSV-1) activity.⁶

Price and Availability

Related Papers

1. Duramycins B and C, two new lanthionine containing antibiotics as inhibitors of phospholipase A2. Structural revision of duramycin and cinnamycin. Fredenhagen, A., et al. J. Antibiot. 43, 1403-1412, (1990)

Documents

Certificate of Analysis

C5241 - Datasheet (107KB)

Safety Information

Personal Protective Equipment	Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
WGK Germany	3
RTECS	GE1745000

Technical information & documentation associated with this product is available in the Safety & Documentation tab.

Articles

Antimicrobial Peptides

With bacterial resistance and emerging infectious diseases becoming potential threats to humans, ribosomally synthesized antimicrobial peptides have become a promising focus area in antibiotic resear...
Chloe McClanahan
BioFiles 2009, 4.3, 4.
Keywords: Antibiotics, Antimicrobials, Antiparasitics, Antivirals, Apoptosis, Cancer, Clinical, Diseases, Environmental, Fermentation, Food Safety, Gene expression, Genetic, Genetics, Infectious Diseases, Microbiology, Peptide synthesis, Pesticides, Respiratory

Papers

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1. Duramycins B and C, two new lanthionine containing antibiotics as inhibitors of phospholipase A2. Structural revision of duramycin and cinnamycin. Fredenhagen, A., et al. J. Antibiot. 43, 1403-1412, (1990)

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2. Nine Post -translational modifications during the biosynthesis of cinnamycin. Okesli, A., et al. J. Am. Chem. Soc. 133, 13753-13760, (2011)

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3. Cloning and engineering of the cinnamycin biosynthetic gene cluster from Streptomyces cinnamoneus cinnamoneus DSM 40005 Widdick, D. A. et al. Proc. Natl. Acad. Sci. U. S. A. 100, 4316-4321, (2003)

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4. Cinnamycin (Ro 09-0198) promotes cell binding and toxicity by inducing transbilayer lipid movement. Makino, A., et al. J. Biol. Chem. 278, 3204-3209, (2003)

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5. Lantibiotics as probes for phosphatidylethanolamine. Zhao, M. Amino Acids 41, 1071-1079, (2011)

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6. Lanthiopeptin, a new peptide effective against herpes simplex virus: Structural determination and comparison with Ro 09-0198, an immunopotentiating peptide. Wakamiya, T., et al. Tetrahedron Lett. 29, 3771-4772, (1988)

Specific binding of Ro 09-0198 (cinnamycin) to phosphatidylethanolamine: a thermodynamic analysis. Machiadze, G., et al. Biochemistry 41, 1965-1971, (2002)

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