Crocacin A
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| Category | Enzyme inhibitors |
| Catalog number | BBF-01079 |
| CAS | 157698-34-5 |
| Molecular Weight | 538.67 |
| Molecular Formula | C31H42N2O6 |
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Description
It is produced by the strain of Chondromyces crocatus sp. Cm c3. It has anti-yeast and filamentous fungal activity. It can inhibit mouse fibroblasts L929 (MIC is 0.2 ng). In the microsomes of the calf's heart, it can interrupt the bc1 segment of electronic transmission, causes redshift of 569nm peak in cytochrome B reduction spectrum.
Specification
| Synonyms | (+)-CrocainA; [(2Z,5Z)-6-((6S,7S,8S,9S)-(2E,4E,10E)-7,9-Dimethoxy-3,6,8-trimethyl-11-phenyl-undeca-2,4,10-trienoylamino)-hexa-2,5-dienoylamino]-acetic acid, methyl ester; Methyl 2-[6-((2E,4E,10E)(6S,7S,9S,8R)-7,9-dimethoxy-3,6,8-trimethyl-11-phenylundeca-2,4,10-trienoylamino)(2Z,5Z)hexa-2,5-dienoylamino]acetate |
| IUPAC Name | methyl 2-[[(2Z,5Z)-6-[[(2E,4E,6S,7S,8R,9S,10E)-7,9-dimethoxy-3,6,8-trimethyl-11-phenylundeca-2,4,10-trienoyl]amino]hexa-2,5-dienoyl]amino]acetate |
| Canonical SMILES | CC(C=CC(=CC(=O)NC=CCC=CC(=O)NCC(=O)OC)C)C(C(C)C(C=CC1=CC=CC=C1)OC)OC |
| InChI | InChI=1S/C31H42N2O6/c1-23(21-29(35)32-20-12-8-11-15-28(34)33-22-30(36)38-5)16-17-24(2)31(39-6)25(3)27(37-4)19-18-26-13-9-7-10-14-26/h7,9-21,24-25,27,31H,8,22H2,1-6H3,(H,32,35)(H,33,34)/b15-11-,17-16+,19-18+,20-12-,23-21+/t24-,25+,27-,31-/m0/s1 |
| InChI Key | XHTUDGVBJDVOEZ-PSXYSELWSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria; Fungi; Yeast |
| Solubility | Soluble in Chloroform, Methanol, Acetone, Ethyl Acetate |
Reference Reading
1. Total synthesis of (+)-crocacin D
Luiz C Dias, Luciana G de Oliveira, Janaína D Vilcachagua, Florian Nigsch J Org Chem. 2005 Mar 18;70(6):2225-34. doi: 10.1021/jo047732k.
[structure: see text] The total synthesis of (+)-crocacin D is described. The convergent asymmetric synthesis relies on the use of a Stille cross-coupling between an (E)-vinyl stannane with an (E)-vinyl iodide to establish the (E,E)-dienamide moiety followed by a mild and efficient copper-catalyzed coupling between (+)-crocacin C and a (Z)-vinyl iodide to establish the challenging (Z)-enamide function.
2. Crocacin, a new electron transport inhibitor from Chondromyces crocatus (myxobacteria). Production, isolation, physico-chemical and biological properties
B Kunze, R Jansen, G Höfle, H Reichenbach J Antibiot (Tokyo). 1994 Aug;47(8):881-6. doi: 10.7164/antibiotics.47.881.
Crocacin was isolated from the biomass of the myxobacterium Chondromyces crocatus, strain Cm c3. It inhibited the growth of a few Gram-positive bacteria and a wide spectrum of yeasts and molds. In beef heart submitochondrial particles, crocacin blocked the electron transport within the bc1-segment (complex III) and caused a red shift in the reduced spectrum of cytochrome b with a maximum at 569 nm.
3. The role of molecular modeling in the design of analogues of the fungicidal natural products crocacins A and D
Patrick J Crowley, Edward A Berry, Thomas Cromartie, Fevzi Daldal, Christopher R A Godfrey, Dong-Woo Lee, Janet E Phillips, Anne Taylor, Russell Viner Bioorg Med Chem. 2008 Dec 15;16(24):10345-55. doi: 10.1016/j.bmc.2008.10.030. Epub 2008 Oct 17.
Extensive molecular modeling based on crystallographic data was used to aid the design of synthetic analogues of the fungicidal naturally occurring respiration inhibitors crocacins A and D, and an inhibitor binding model to the mammalian cytochrome bc(1) complex was constructed. Simplified analogues were made which showed high activity in a mitochondrial beef heart respiration assay, and which were also active against certain plant pathogens in glasshouse tests. A crystal structure was obtained of an analogue of crocacin D bound to the chicken heart cytochrome bc(1) complex, which validated the binding model and which confirmed that the crocacins are a new class of inhibitor of the cytochrome bc(1) complex.
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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 ╳
