Cochinmicin I
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| Category | Others |
| Catalog number | BBF-00374 |
| CAS | 143728-97-6 |
| Molecular Weight | 889.90 |
| Molecular Formula | C46H47N7O12 |
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Description
Cochinmicin I is produced by the strain of Microbispora sp.. Cochinmicin I has the antagonistic effect of endothelin and it is the most active of all components.
Specification
| IUPAC Name | N-[(2S)-1-[[(3R,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]-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=CN6 |
| InChI | InChI=1S/C46H47N7O12/c1-24-40(58)52-38(28-18-30(54)22-31(55)19-28)45(63)53-39(29-20-32(56)23-33(57)21-29)46(64)65-25(2)37(44(62)50-35(42(60)48-24)16-26-10-5-3-6-11-26)51-43(61)36(17-27-12-7-4-8-13-27)49-41(59)34-14-9-15-47-34/h3-15,18-25,35-39,47,54-57H,16-17H2,1-2H3,(H,48,60)(H,49,59)(H,50,62)(H,51,61)(H,52,58)(H,53,63)/t24-,25-,35-,36+,37-,38-,39-/m1/s1 |
| InChI Key | BAIAJPQVHAPGNS-BTTFJQTNSA-N |
Properties
| Solubility | Soluble in Methanol |
Reference Reading
1. Total Synthesis and Biosynthesis of Cyclodepsipeptide Cochinmicin I
Romina Schnegotzki, Vincent Wiebach, Marina Sánchez-Hidalgo, Marcel Tietzmann, Andreas B Zur Bonsen, Olga Genilloud, Roderich D Süssmuth Org Lett. 2022 Apr 1;24(12):2344-2348. doi: 10.1021/acs.orglett.2c00525. Epub 2022 Mar 21.
Phenylglycines are building blocks of many non-ribosomally synthesized peptides. The dihydroxyphenylglycine-containing cyclodepsipeptide cochinmicin I exhibits endothelin receptor antagonist activity. Therefore, it represents an interesting and synthetically challenging molecule because of the racemization-prone nature of dihydroxyphenylglycine. We present the total synthesis of cochinmicin I and the non-natural derivative cochinmicin VI and describe the identification and assignment of the cochinmicin (cmn) biosynthesis gene cluster, encoding a five-module non-ribosomal peptide synthetase for cochinmicin assembly.
2. 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.
3. 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.
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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 ╳
