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安全信息

C5241

Sigma-Aldrich

Cinnamycin

from Streptomyces cinnamoneus, ≥95% (HPLC)

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别名:
Ro 09-0198
经验公式（希尔记法）:
C89H125N25O25S3
CAS号:
110655-58-8
分子量:
2041.29
MDL编号:
MFCD01770867
NACRES:
NA.77

生物来源

Streptomyces cinnamoneus

质量水平

200

检测方案

≥95% (HPLC)

形式

solid

溶解性

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

抗生素抗菌谱

fungi

作用机制

cell membrane | interferes

储存温度

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 key

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

一般描述

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

应用

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.

储存分类代码

11 - Combustible Solids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

Eyeshields, Gloves, type N95 (US)

法规信息

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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
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
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
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