![1-[(4R,5R)-4,5-dihydroxy-L-ornithine]-Echinocandin B](/upload/banner/navi-3853.jpg)
1-[(4R,5R)-4,5-dihydroxy-L-ornithine]-Echinocandin B
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![1-[(4R,5R)-4,5-dihydroxy-L-ornithine]-Echinocandin B](https://resource.bocsci.com/structure/79411-15-7.gif)
| Category | Antifungal |
| Catalog number | BBF-05835 |
| CAS | 79411-15-7 |
| Molecular Weight | 797.81 |
| Molecular Formula | C34H51N7O15 |
| Purity | 95% |
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Description
1-[(4R,5R)-4,5-dihydroxy-L-ornithine]-Echinocandin B is an intermediate of Anidulafungin, an echinocandin antifungal drug.
Specification
| Related CAS | 1029890-89-8 (hydrochloride) |
| Synonyms | Echinocandin B nucleus; (2R,6S,9S,11R,12R,14aS,15S,16S,20S,23S,25aS)-9-Amino-23-[(1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-2,11,12,15-tetrahydroxy-6,20-bis[(1R)-1-hydroxyethyl]-16-methylhexadecahydro-1H-dipyrrolo[2,1-c:2',1'-l][1,4,7,10,13,16]hexaazacyclohenicosine-5,8,14,19,22,25(9H,25aH)-hexone; Echinocandin B, 1-[(4R,5R)-4,5-dihydroxy-L-ornithine]- |
| Storage | Store at -20°C under inert atmosphere |
| IUPAC Name | (3S,6S,9S,11R,15S,18S,20R,21R,24S,25S,26S)-18-amino-6-[(1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-11,20,21,25-tetrahydroxy-3,15-bis[(1R)-1-hydroxyethyl]-26-methyl-1,4,7,13,16,22-hexazatricyclo[22.3.0.09,13]heptacosane-2,5,8,14,17,23-hexone |
| Canonical SMILES | CC1CN2C(C1O)C(=O)NC(C(CC(C(=O)NC(C(=O)N3CC(CC3C(=O)NC(C(=O)NC(C2=O)C(C)O)C(C(C4=CC=C(C=C4)O)O)O)O)C(C)O)N)O)O |
| InChI | InChI=1S/C34H51N7O15/c1-12-10-41-24(25(12)47)32(54)39-30(52)20(46)9-18(35)28(50)36-21(13(2)42)33(55)40-11-17(45)8-19(40)29(51)38-23(31(53)37-22(14(3)43)34(41)56)27(49)26(48)15-4-6-16(44)7-5-15/h4-7,12-14,17-27,30,42-49,52H,8-11,35H2,1-3H3,(H,36,50)(H,37,53)(H,38,51)(H,39,54)/t12-,13+,14+,17+,18-,19-,20+,21-,22-,23-,24-,25-,26-,27-,30+/m0/s1 |
| InChI Key | BLKJKIJFNJAQIZ-UMDMRRTDSA-N |
Properties
| Appearance | Off-white Solid |
| Boiling Point | 1330.8±65.0°C (Predicted) |
| Melting Point | >190°C (dec.) |
| Density | 1.60±0.06 g/cm3 (Predicted) |
| Solubility | Soluble in DMSO (Slightly), Methanol (Slightly), Water (Slightly, Sonicated) |
Reference Reading
1.Genomics-driven discovery of the pneumocandin biosynthetic gene cluster in the fungus Glarea lozoyensis.
Chen L1, Yue Q, Zhang X, Xiang M, Wang C, Li S, Che Y, Ortiz-López FJ, Bills GF, Liu X, An Z. BMC Genomics. 2013 May 20;14:339. doi: 10.1186/1471-2164-14-339.
BACKGROUND: The antifungal therapy caspofungin is a semi-synthetic derivative of pneumocandin B0, a lipohexapeptide produced by the fungus Glarea lozoyensis, and was the first member of the echinocandin class approved for human therapy. The nonribosomal peptide synthetase (NRPS)-polyketide synthases (PKS) gene cluster responsible for pneumocandin biosynthesis from G. lozoyensis has not been elucidated to date. In this study, we report the elucidation of the pneumocandin biosynthetic gene cluster by whole genome sequencing of the G. lozoyensis wild-type strain ATCC 20868.
2.Echinocandins: production and applications.
Emri T1, Majoros L, Tóth V, Pócsi I. Appl Microbiol Biotechnol. 2013 Apr;97(8):3267-84. doi: 10.1007/s00253-013-4761-9. Epub 2013 Mar 6.
The first echinocandin-type antimycotic (echinocandin B) was discovered in the 1970s. It was followed by the isolation of more than 20 natural echinocandins. These cyclic lipo-hexapeptides are biosynthesized on non-ribosomal peptide synthase complexes by different ascomycota fungi. They have a unique mechanism of action; as non-competitive inhibitors of β-1,3-glucan synthase complex they target the fungal cell wall. Results of the structure-activity relationship experiments let us develop semisynthetic derivatives with improved properties. Three cyclic lipohiexapeptides (caspofungin, micafungin and anidulafungin) are currently approved for use in clinics. As they show good fungicidal (Candida spp.) or fungistatic (Aspergillus spp.) activity against the most important human pathogenic fungi including azole-resistant strains, they are an important addition to the antifungal armamentarium. Some evidence of acquired resistance against echinocandins has been detected among Candida glabrata strains in recent years, which enhanced the importance of data collected on the mechanism of acquired resistance developing against the echinocandins.
3.Mutagenesis breeding of high echinocandin B producing strain and further titer improvement with culture medium optimization.
Zou SP1, Zhong W1, Xia CJ1, Gu YN1, Niu K1, Zheng YG2, Shen YC1. Bioprocess Biosyst Eng. 2015 Oct;38(10):1845-54. doi: 10.1007/s00449-015-1425-4. Epub 2015 Jun 20.
A combination of microbial strain improvement and statistical optimization is investigated to maximize echinocandin B (ECB) production from Aspergillus nidulans ZJB-0817. A classical sequential mutagenesis was studied first by using physical (ultraviolet irradiation at 254 nm) and chemical mutagens (lithium chloride and sodium nitrite). Mutant strain ULN-59 exhibited 2.1-fold increase in ECB production to 1583.1 ± 40.9 mg/L when compared with the parent strain (750.8 ± 32.0 mg/L). This is the first report where mutagenesis is applied in Aspergillus to improve ECB production. Further, fractional factorial design and central composite design were adopted to optimize the culture medium for increasing ECB production by the mutant ULN-59. Results indicated that four culture media including peptone, K2HPO4, mannitol and L-ornithine had significant effects on ECB production. The optimized medium provided another 1.4-fold increase in final ECB concentration to 2285.
4.Preparative separation of echinocandin B from Aspergillus nidulans broth using macroporous resin adsorption chromatography.
Zou SP1, Liu M1, Wang QL1, Xiong Y1, Niu K1, Zheng YG2, Shen YC1. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Jan 26;978-979:111-7. doi: 10.1016/j.jchromb.2014.11.028. Epub 2014 Dec 4.
Echinocandin B (ECB), an echinocandin type of lipopeptide antibiotic produced by Aspergillus nidulans, is a precursor for the synthesis of novel anti-fungal drug - anidulafungin. In this work, a separation strategy involving one-step macroporous resin adsorption chromatography was established for ECB purification from Aspergillus nidulans CCTCC M 2010275 fermentation broth. Among nine macroporous resin adsorbents tested, the non-polar resin HP-20 had the best adsorption and desorption performance. The static equilibrium adsorption data fitted well with the Langmuir equation, and the adsorption kinetic followed the pseudo-second order model. The separation parameters of ECB from broth were optimised by dynamic adsorption/desorption experiments with the column packed with HP-20 resin. Under optimal conditions, the purity increased by 3.8-fold from 23.2% in broth to 88.5% in eluent with 87.1% recovery yield by a one-step treatment. Our study provided a one-step and effective method for large-scale production of ECB, and offered references for separating other echinocandins from broth.
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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
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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
