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C5241

Sigma-Aldrich

Cinnamycin

from Streptomyces cinnamoneus, ≥95% (HPLC)

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Synonym(s):
Lanthiopeptin, NSC-71936, Ro 09-0198
Empirical Formula (Hill Notation):
C89H125N25O25S3
CAS Number:
110655-58-8
Molecular Weight:
2041.29
MDL number:
MFCD01770867
NACRES:
NA.77

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

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.

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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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
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
N Naruse et al.
The Journal of antibiotics, 42(6), 837-845 (1989-06-01)
A strain of Streptoverticillium cinnamoneum produced a peptide antibiotic named lanthiopeptin, which contained four unusual amino acids, erythro-beta-hydroxyaspartic acid, mesolanthionine, threo-beta-methyllanthionine and lysinoalanine. Lanthiopeptin showed antiviral activity against herpes simplex virus type 1 KOS strain infection in Vero cells by
Utako Kato et al.
The Journal of biological chemistry, 277(40), 37855-37862 (2002-07-23)
Ro09-0198 (Ro) is a tetracyclic peptide antibiotic that binds specifically to phosphatidylethanolamine (PE) and causes cytolysis. To investigate the molecular basis of transbilayer movement of PE in biological membranes, we have isolated a series of budding yeast mutants that are
S Y Choung et al.
Biochimica et biophysica acta, 940(2), 171-179 (1988-05-24)
Ro09-0198, a cyclic peptide isolated from culture filtrates of Streptoverticillium griseoverticillatum, induced lysis of erythrocytes. Preincubation of the peptide with phosphatidylethanolamine reduced the hemolytic activity, whereas other phospholipids present in erythrocytes in nature had no effect. A study of the
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