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CN

C5241

Sigma-Aldrich

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
MDL number:
MFCD01770867
UNSPSC Code:
51111800
NACRES:
NA.77

Key Documents

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Product Name

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

biological source

Streptomyces cinnamoneus

Quality Level

200

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

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

Related Categories

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

General description

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

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000265554
0000261309
0000261309
0000220014
0000265554

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Nine post-translational modifications during the biosynthesis of cinnamycin
O?kesli A, et al.
Journal of the American Chemical Society, 133(34), 13753-13760 (2011)
M Lipták et al.
Biological mass spectrometry, 23(11), 701-706 (1994-11-01)
Four lantibiotics namely epidermin, gallidermin, lanthiopeptin and mersacidin, have been studied by fast atom bombardment mass spectrometry. The molecular ion clusters of these compounds can be detected with reasonable abundance. The low-mass regions of the spectra show the presence of
K Emoto et al.
Experimental cell research, 232(2), 430-434 (1997-05-01)
In the early stages of apoptosis, phosphatidylserine (PS) is translocated from the inner side of the plasma membrane to the outer layer, which allows phagocytes to recognize and engulf the apoptotic cells. In this study we have analyzed the cell
K Wakamatsu et al.
Biochemistry, 29(1), 113-118 (1990-01-09)
Ro09-0198 is a peptide antibiotic and immunopotentiator produced by Streptoverticillium griseoverticillatum which exhibits antitumor and antimicrobial activities. The chemical structure has been determined [Kessler et al. (1988) Helv. Chim. Acta 71, 1924-1929; Wakamiya et al. (1988) Tetrahedron Lett. 37, 4771-4772].
Sophie Chen et al.
Traffic (Copenhagen, Denmark), 7(11), 1503-1517 (2006-09-08)
Drs2p, a P-type adenosine triphosphatase required for a phosphatidylserine (PS) flippase activity in the yeast trans Golgi network (TGN), was first implicated in protein trafficking by a screen for mutations synthetically lethal with arf1 (swa). Here, we show that SWA4
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