C5241

Cinnamycin

from Streptomyces cinnamoneus, ≥95% (HPLC)

• Synonym(e): Lanthiopeptin, NSC-71936, Ro 09-0198
• Empirische Formel (Hill-System): C₈₉H₁₂₅N₂₅O₂₅S₃
• CAS-Nummer: 110655-58-8
• Molekulargewicht: 2041.29
• MDL-Nummer: MFCD01770867
• UNSPSC-Code: 51111800
• NACRES: NA.77

Eigenschaften

• Biologische Quelle: Streptomyces cinnamoneus
• Qualitätsniveau: 200
• Assay: ≥95% (HPLC)
• Form: solid
• Löslichkeit: DMSO: 10 mg/mL; acetonitrile: water (1:1): 5 mg/mL (requires heating)
• Wirkungsspektrum von Antibiotika: fungi
• Wirkungsweise: cell membrane | interferes
• Lagertemp.: 2-8°C
• SMILES String: S1[C@@H](C2NC(=O)[C@@H](NC(=O)CNC(=O)[C@@H](NC(=O)[C@H]3NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H]5NC(=O)[C@@H](NC(=O)[C@H]7N(CCC7)C(=O)CNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](C1)N)CCCN\C(=N/[H])\N)CCC(=O)N)CS
• 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(32-46-18-8-5-9-19-46)103-78(127)57(106-80(60)129)36-95-29-15-14-24-52(87(136)137)102-85(134)67(112-77(126)56(35-63(92)116)99-64(117)37-97-83(132)69(113-81(59)130)70(119)88(138)139)44(3)141-39-49(90)71(120)100-50(25-16-30-96-89(93)94)73(122)101-51(74(123)107-58)27-28-62(91)115/h5-13,18-23,43-45,49-61,66-70,95,119H,14-17,24-42,90H2,1-4H3,(H2,91,115)(H2,92,116)(H,97,132)(H,98,121)(H,99,117)(H,100,120)(H,101,122)(H,102,134)(H,103,127)(H,104,131)(H,105,135)(H,106,129)(H,107,123)(H,108,128)(H,109,133)(H,110,124)(H,111,125)(H,112,126)(H,113,130)(H,136,137)(H,138,139)(H4,93,94,96)/t44-,45?,49+,50+,51+,52+,53+,54+,55+,56+,57+,58+,59+,60+,61+,66+,67?,68+,69+,70-/m1/s1
• InChIKey: QJDWKBINWOWJNZ-IDGBIKHQSA-N

Beschreibung

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

Allgemeine Beschreibung

Cinnamycin is synthesized after proteolytic cleavage from core peptide and takes up a compact globular structure.[1]

Anwendung

Cinnamycin has been used in cinnamycin senstivity assay in mouse embryonic fibroblasts (MEFs).[2]

Biochem./physiol. Wirkung

Cinnamycin based analogs may be useful in treating cystic fibrosis or Clostridium infections.[1]

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. The unique receptor for Cinnamycin, phosphatidylethanolamine (PE), is located on the inner leaflet of the plasma membrane. Cinnamycin induces transbilayer lipid movement leading to the exposure of PE to the outer leaflet of the plasma membrane. The interaction of Cinnamycin with PE provides a tool for PE monitoring. Cinnamycin is active against Gram-positive rods such as Bacilli, Clostyridium and Mycobacterium, causing cell wall biosynthesis stress.
Cinnamycin, like other lantibiotics, was also reported to inhibit phospholipase A2 (PLA2). It was suggested as an alternative treatment for atherosclerosis through its ability to inhibit PLA2 by binding to its substrate PE. Moreover, Cinnamycin was found to inhibit Herpes simplex virus (HSV-1) activity.

Cinnamycin is a tetracyclic polypeptide antibiotic of 19 amino acids.

Sicherheitshinweise

• Lagerklassenschlüssel: 11 - Combustible Solids
• WGK: WGK 3
• Flammpunkt (°F): Not applicable
• Flammpunkt (°C): Not applicable
• Persönliche Schutzausrüstung: Eyeshields, Gloves, type N95 (US)