Crocacin B
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| Category | Enzyme inhibitors |
| Catalog number | BBF-01080 |
| CAS | 237425-37-5 |
| Molecular Weight | 524.65 |
| Molecular Formula | C30H40N2O6 |
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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 | [[(2Z,5Z)-6-[[(2E,4E,6S,7S,8R,9S,10E)-7,9-Dimethoxy-3,6,8-trimethyl-1-oxo-11-phenyl-2,4,10-undecatrienyl]amino]-1-oxo-2,5-hexadienyl]amino]acetic acid; 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]acetic acid |
| IUPAC Name | 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]acetic acid |
| Canonical SMILES | CC(C=CC(=CC(=O)NC=CCC=CC(=O)NCC(=O)O)C)C(C(C)C(C=CC1=CC=CC=C1)OC)OC |
| InChI | InChI=1S/C30H40N2O6/c1-22(20-28(34)31-19-11-7-10-14-27(33)32-21-29(35)36)15-16-23(2)30(38-5)24(3)26(37-4)18-17-25-12-8-6-9-13-25/h6,8-20,23-24,26,30H,7,21H2,1-5H3,(H,31,34)(H,32,33)(H,35,36)/b14-10-,16-15+,18-17+,19-11-,22-20+/t23-,24+,26-,30-/m0/s1 |
| InChI Key | KSYRCWWRVVIIEX-XUBYDZNKSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria; Fungi; Yeast |
| Solubility | Soluble in Methanol |
Reference Reading
1. Biosynthesis of crocacin involves an unusual hydrolytic release domain showing similarity to condensation domains
Stefan Müller, Shwan Rachid, Thomas Hoffmann, Frank Surup, Carsten Volz, Nestor Zaburannyi, Rolf Müller Chem Biol. 2014 Jul 17;21(7):855-65. doi: 10.1016/j.chembiol.2014.05.012. Epub 2014 Jun 26.
The crocacins are potent antifungal and cytotoxic natural compounds from myxobacteria of the genus Chondromyces. Although total synthesis approaches have been reported, the molecular and biochemical basis guiding the formation of the linear crocacin scaffold has remained unknown. Along with the identification and functional analysis of the crocacin biosynthetic gene cluster from Chondromyces crocatus Cm c5, we here present the identification and biochemical characterization of an unusual chain termination domain homologous to condensation domains responsible for hydrolytic release of the product from the assembly line. In particular, gene inactivation studies and in vitro experiments using the heterologously produced domain CroK-C2 confirm this surprising role giving rise to the linear carboxylic acid. Additionally, we determined the kinetic parameters of CroK-C2 by monitoring hydrolytic cleavage of the substrate mimic N-acetylcysteaminyl-crocacin B using an innovative high-performance liquid chromatography mass spectrometry-based assay.
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.
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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 ╳
