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Merck
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Key Documents

C5241

Sigma-Aldrich

Cinnamycin

from Streptomyces cinnamoneus, ≥95% (HPLC)

别名:

Ro 09-0198

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About This Item

经验公式（希尔记法）:
C89H125N25O25S3
CAS号:
110655-58-8
分子量:
2041.29
MDL號碼:
MFCD01770867
分類程式碼代碼:
51111800
NACRES:
NA.77

生物源

Streptomyces cinnamoneus

品質等級

200

化驗

≥95% (HPLC)

形狀

solid

溶解度

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

抗生素活性譜

fungi

作用方式

cell membrane | interferes

儲存溫度

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 密鑰

QJDWKBINWOWJNZ-IDGBIKHQSA-N

相关类别

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

一般說明

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

應用

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

生化／生理作用

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.

儲存類別代碼

11 - Combustible Solids

水污染物質分類（WGK）

WGK 3

閃點（°F）

Not applicable

閃點（°C）

Not applicable

個人防護裝備

Eyeshields, Gloves, type N95 (US)

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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
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
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
Upregulated function of mitochondria-associated ER membranes in Alzheimer disease
Area-Gomez E, et al.
The Embo Journal, 31(21), 4106-4123 (2012)
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].
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