Cochinmicin II
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| Category | Others |
| Catalog number | BBF-00375 |
| CAS | 143728-98-7 |
| Molecular Weight | 924.35 |
| Molecular Formula | C46H46ClN7O12 |
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Description
Cochinmicin II is produced by the strain of Microbispora sp.. Cochinmicin II has the antagonistic effect of endothelin.
Specification
| IUPAC Name | N-[(2S)-1-[[(3S,6R,9R,12R,15R,16R)-12-benzyl-3,6-bis(3,5-dihydroxyphenyl)-9,16-dimethyl-2,5,8,11,14-pentaoxo-1-oxa-4,7,10,13-tetrazacyclohexadec-15-yl]amino]-1-oxo-3-phenylpropan-2-yl]-5-chloro-1H-pyrrole-2-carboxamide |
| Canonical SMILES | CC1C(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)O1)C2=CC(=CC(=C2)O)O)C3=CC(=CC(=C3)O)O)C)CC4=CC=CC=C4)NC(=O)C(CC5=CC=CC=C5)NC(=O)C6=CC=C(N6)Cl |
| InChI | InChI=1S/C46H46ClN7O12/c1-23-40(59)53-38(27-17-29(55)21-30(56)18-27)45(64)54-39(28-19-31(57)22-32(58)20-28)46(65)66-24(2)37(44(63)51-34(42(61)48-23)15-25-9-5-3-6-10-25)52-43(62)35(16-26-11-7-4-8-12-26)50-41(60)33-13-14-36(47)49-33/h3-14,17-24,34-35,37-39,49,55-58H,15-16H2,1-2H3,(H,48,61)(H,50,60)(H,51,63)(H,52,62)(H,53,59)(H,54,64)/t23-,24-,34-,35+,37-,38-,39+/m1/s1 |
| InChI Key | SHHDTFPTYUGWHB-LSTCLERCSA-N |
Properties
| Solubility | Soluble in Methanol |
Reference Reading
1. Cyclodepsipeptides produced by actinomycetes inhibit cyclic-peptide-mediated quorum sensing in Gram-positive bacteria
Said E Desouky, Akane Shojima, Ravindra Pal Singh, Takahisa Matsufuji, Yasuhiro Igarashi, Takashi Suzuki, Tohru Yamagaki, Ken-Ichi Okubo, Kaori Ohtani, Kenji Sonomoto, Jiro Nakayama FEMS Microbiol Lett. 2015 Jul;362(14):fnv109. doi: 10.1093/femsle/fnv109. Epub 2015 Jul 5.
Cyclic peptides are commonly used as quorum-sensing autoinducers in Gram-positive Firmicutes bacteria. Well-studied examples of such molecules are thiolactone and lactone, used to regulate the expression of a series of virulence genes in the agr system of Staphylococcus aureus and the fsr system of Enterococcus faecalis, respectively. Three cyclodepsipeptides WS9326A, WS9326B and cochinmicin II/III were identified as a result of screening actinomycetes culture extracts for activity against the agr/fsr system. These molecules are already known as receptor antagonists, the first two for tachykinin and the last one for endothelin. WS9326A also inhibited the transcription of pfoA regulated by the VirSR two-component system in Clostridium perfringens. Receptor-binding assays using a fluorescence-labeled autoinducer (FITC-GBAP) showed that WS9326A and WS9326B act as receptor antagonists in this system. In addition, an ex vivo assay showed that WS9326B substantially attenuated the toxicity of S. aureus for human corneal epithelial cells. These results suggest that these three natural cyclodepsipeptides have therapeutic potential for targeting the cyclic peptide-mediated quorum sensing of Gram-positive pathogens.
2. Cochinmicins, novel and potent cyclodepsipeptide endothelin antagonists from a Microbispora sp. II. Structure determination
D Zink, O D Hensens, Y K Lam, R Reamer, J M Liesch J Antibiot (Tokyo). 1992 Nov;45(11):1717-22. doi: 10.7164/antibiotics.45.1717.
Cochinmicins I, II, and III are competitive endothelin antagonists produced by Microbispora sp. ATCC 55140. The cochinmicins are cyclic depsipeptides containing six alpha-amino acids and a pyrrolecarboxylic acid. Based upon MS, 1D and 2D NMR, and LC data, the structures and absolute stereochemistries of the cochinmicins have been assigned. All three components have the same basic sequence and contain one equivalent each of D-allo-threonine, D-alanine, L-phenylalanine, D-phenylalanine, 5-chloropyrrole-2-carboxylic acid (or pyrrole-2-carboxylic acid in cochinmicin I), plus two equivalents of 3,5-dihydroxyphenylglycine (DHPG). The phenylalanine residues were differentiated via a methanolysis product which contained only one of the phenylalanine residues. Both DHPG residues have the D configuration in the more active cochinmicins I and III. Cochinmicin II contains both D- and L-DHPG and these residues have been differentiated in the sequence based upon 1H NMR data.
3. Cochinmicins, novel and potent cyclodepsipeptide endothelin antagonists from a Microbispora sp. I. Production, isolation, and characterization
Y K Lam, D L Williams Jr, J M Sigmund, M Sanchez, O Genilloud, Y L Kong, S Stevens-Miles, L Huang, G M Garrity J Antibiot (Tokyo). 1992 Nov;45(11):1709-16. doi: 10.7164/antibiotics.45.1709.
Cochinmicins I, II, III are novel peptolides produced in submerged-fermentation cultures of Microbispora sp. ATCC 55140. These closely related compounds are separated by HPLC and are novel competitive endothelin antagonists. Cochinmicins II and III are stereoisomeric to each other. Cochinmicin I is the deschloro analog of cochinmicin III.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
