Crocacin D
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| Category | Enzyme inhibitors |
| Catalog number | BBF-01082 |
| CAS | 237425-39-7 |
| Molecular Weight | 540.69 |
| Molecular Formula | C31H44N2O6 |
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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 | (+)-Crocacin D |
| IUPAC Name | methyl 2-[[(Z)-6-[[(2E,4E,6S,7S,8R,9S,10E)-7,9-dimethoxy-3,6,8-trimethyl-11-phenylundeca-2,4,10-trienoyl]amino]hex-5-enoyl]amino]acetate |
| Canonical SMILES | CC(C=CC(=CC(=O)NC=CCCCC(=O)NCC(=O)OC)C)C(C(C)C(C=CC1=CC=CC=C1)OC)OC |
| InChI | InChI=1S/C31H44N2O6/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/h7,9-10,12-14,16-21,24-25,27,31H,8,11,15,22H2,1-6H3,(H,32,35)(H,33,34)/b17-16+,19-18+,20-12-,23-21+/t24-,25+,27-,31-/m0/s1 |
| InChI Key | YIOSSWUAQNGRSJ-NRHCNNMKSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria; Fungi; Yeast |
| Solubility | Soluble in Methanol |
Reference Reading
1. Synthesis of (+)-crocacin D and simplified bioactive analogues
Adele E Pasqua, Frank D Ferrari, James J Crawford, William G Whittingham, Rodolfo Marquez Bioorg Med Chem. 2015 Mar 1;23(5):1062-8. doi: 10.1016/j.bmc.2015.01.008. Epub 2015 Jan 10.
The total synthesis of (+)-crocacin D has been achieved in 15 steps (9 isolated intermediates) and 14% overall yield from commercially available starting materials and using (+)-crocacin C as a key intermediate. A number of simplified analogues and their biological activities are also reported.
2. 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.
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 ╳
