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Merck

C5241

Cinnamycin

From Streptomyces cinnamoneus, ≥95% (HPLC), peptide antibiotic, solid

Synonym(s):

Lanthiopeptin, NSC-71936, Ro 09-0198

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About This Item

Empirical Formula (Hill Notation):
C89H125N25O25S3
CAS Number:
110655-58-8
Molecular Weight:
2041.29
UNSPSC Code:
51111800
NACRES:
NA.77
MDL number:
MFCD01770867

Key Documents

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Product Name

Cinnamycin, from Streptomyces cinnamoneus, ≥95% (HPLC)

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

InChI key

QJDWKBINWOWJNZ-IDGBIKHQSA-N

biological source

Streptomyces cinnamoneus

assay

≥95% (HPLC)

form

solid

solubility

DMSO: 10 mg/mL
acetonitrile: water (1:1): 5 mg/mL (requires heating)

antibiotic activity spectrum

fungi

mode of action

cell membrane | interferes

storage temp.

2-8°C

Quality Level

200

Related Categories

Application

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

Biochem/physiol Actions

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

General description

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

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000265554
0000261309
0000261309
0000220014
0000265554

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K Emoto et al.
Proceedings of the National Academy of Sciences of the United States of America, 93(23), 12867-12872 (1996-11-12)
Ro09-0198 is a tetracyclic polypeptide of 19 amino acids that recognizes strictly the structure of phosphatidylethanolamine (PE) and forms a tight equimolar complex with PE on biological membranes. Using the cyclic peptide coupled with fluorescence-labeled streptavidin, we have analyzed the
Y Aoki et al.
Journal of biochemistry, 116(2), 291-297 (1994-08-01)
Ro09-0198 is a cyclic peptide isolated from Streptoverticillium griseoverticillatum which recognizes strictly the structure of phosphatidylethanolamine (PE) and forms an equimolar complex with the phospholipid on biological membranes. To use the peptide as a probe for analyzing the transbilayer movement
W P Vermeulen et al.
Molecular membrane biology, 13(2), 95-102 (1996-04-01)
Decreasing the size of the outer leaflet pool of phosphatidylethanolamine (PE) in the erythrocyte membrane by treatment of intact cells with either phospholipase A2, or trinitrobenzenesulphonic acid (TNBS), causes a corresponding decrease in Mg(2+)-ATPase activity as determined in their respective
Keiko Takagi et al.
Biochemical and biophysical research communications, 417(1), 490-494 (2011-12-20)
It is widely accepted that phosphatidylethanolamine (PE) is enriched in the cytosolic leaflet of the eukaryotic plasma membranes. To identify genes involved in the establishment and regulation of the asymmetric distribution of PE on the plasma membrane, we screened the
A Ikemoto et al.
Archives of biochemistry and biophysics, 364(1), 67-74 (1999-03-24)
We have shown previously that docosahexaenoic acid (DHA) promotes and arachidonic acid (AA) suppresses neurite outgrowth of PC12 cells induced by nerve growth factor (NGF) and that incorporation of [3H]ethanolamine into phosphatidylethanolamine (PE) is suppressed in PC12 cells by AA
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