A tetracyclic lantibiotic
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Cinnamycin

Item No. 20136

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
L-cysteinyl-L-arginyl-L-glutaminyl-D-cysteinyl-L-cysteinyl-3-aminoalanyl-L-phenylalanylglycyl-L-prolyl-L-phenylalanyl-(2S,3S)-2-amino-3-mercaptobutanoyl-L-phenylalanyl-L-valyl-L-cysteinyl-(3R)-3-hydroxy-L-a-aspartylglycyl-L-asparaginyl-(2S,3S)-2-amino-3-mercaptobutanoyl-L-lysine,cyclic (1→18),(4→14),(5→11)-tris(thioether),cyclic (6→19)-imine
CAS Number
110655-58-8
Synonyms
  • Lanthiopeptin
  • NSC 71936
  • Ro 09-0198
Molecular Formula
C89H125N25O25S3
Formula Weight
2041.3
Purity
≥85%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: SolubleDMSO: SolubleEthanol: SolubleMethanol: Soluble
SMILES
O=C([C@H](C(C)C)NC([C@H](CC1=CC=CC=C1)NC([C@@H]([C@H](C)SC[C@H](NC([C@H](N2)CSC3)=O)C4=O)NC([C@H](CC5=CC=CC=C5)NC([C@H]6N(C(CNC([C@@H](NC([C@H](CNCCCC[C@@H](C(O)=O)N7)N4)=O)CC8=CC=CC=C8)=O)=O)CCC6)=O)=O)=O)=O)N[C@@H]3C(N[C@@H]([C@@H](O)C(O)=O)C(NCC(N
InChi Code
InChI=1S/C89H125N25O25S3/c1-43(2)66-84(133)109-59-41-140-40-58-79(128)108-60-42-142-45(4)68(86(135)105-55(75(124)110-66)34-48-22-12-7-13-23-48)111-76(125)54(33-47-20-10-6-11-21-47)104-82(131)61-26-17-31-114(61)65(118)38-98-72(121)53(32-46-18-8-5-9-19
InChi Key
QJDWKBINWOWJNZ-OURZNGJWSA-N
Origin
Bacterium/Streptomyces sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Cinnamycin is tetracyclic lantibiotic produced from S. cinnamoneus that contains four unusual amino acids: erythro-β-hydroxyaspartic acid, mesolanthionine, threo-β-methyllanthionine, and lysinoalanine.1 Cinnamycin has demonstrated antiviral activity against herpes simplex virus type 1 KOS strain infection in Vero cells via a cytopathic effect reduction assay.1 Cinnamycin recognizes the structure of phosphatidylethanolamine and forms an equimolar complex with the phospholipid on biological membranes.2 This peptide has been used as a probe for analyzing the transbilayer movement of phosphatidylethanolamine.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Naruse, N., Tenmyo, O., Tomita, K., et al. Lanthiopeptin, a new peptide antibiotic. Production, isolation and properties of lanthiopeptin. J. Antibiot. (Tokyo) 42(6), 837-845 (1989).

    2. Brötz, H., and Sahl, H.G. New insights into the mechanism of action of lantibiotics—diverse biological effects by binding to the same molecular target. J. Antimicrob. Chemother. 46(1), 1-6 (2000).

    3. Aoki, Y., Uenaka, T., Aoki, J., et al. A novel peptide probe for studying the transbilayer movement of phosphatidylethanolamine. J. Bio. Chem. 116(2), 291 - 297 (1994).