Polyoxin A
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-02580 |
| CAS | 19396-03-3 |
| Molecular Weight | 616.53 |
| Molecular Formula | C23H32N6O14 |
| Purity | 95% |
Online Inquiry
Description
Polyoxin A is a nucleoside antifungal antibiotic produced by Str. cacaor var. asoensis and Str. piomogenus.
Specification
| Synonyms | (S-(E))-1-(5-((2-Amino-5-O-(aminocarbonyl)-2-deoxy-L-xylonoyl)amino)-1,5-dideoxy-1-(3,4-dihydro-5-(hydroxymethyl)-2,4-dioxo-1(2H)-pyrimidinyl)-beta-D-allofuranuronoyl)-3-ethylidene-2-azetidinecarboxylic acid |
| IUPAC Name | (2S,3Z)-1-[(2S)-2-[[(2S,3S,4S)-2-amino-5-carbamoyloxy-3,4-dihydroxypentanoyl]amino]-2-[(2R,3S,4R,5R)-3,4-dihydroxy-5-[5-(hydroxymethyl)-2,4-dioxopyrimidin-1-yl]oxolan-2-yl]acetyl]-3-ethylideneazetidine-2-carboxylic acid |
| Canonical SMILES | CC=C1CN(C1C(=O)O)C(=O)C(C2C(C(C(O2)N3C=C(C(=O)NC3=O)CO)O)O)NC(=O)C(C(C(COC(=O)N)O)O)N |
| InChI | InChI=1S/C23H32N6O14/c1-2-7-3-28(12(7)21(38)39)19(37)11(26-18(36)10(24)13(32)9(31)6-42-22(25)40)16-14(33)15(34)20(43-16)29-4-8(5-30)17(35)27-23(29)41/h2,4,9-16,20,30-34H,3,5-6,24H2,1H3,(H2,25,40)(H,26,36)(H,38,39)(H,27,35,41)/b7-2-/t9-,10-,11-,12-,13+,14-,15+,16+,20+/m0/s1 |
| InChI Key | PQAGMWMKVWTHJU-ATETYRDMSA-N |
Properties
| Appearance | Colorless Needle Crystal |
| Antibiotic Activity Spectrum | fungi |
| Melting Point | 180°C (dec.) |
| Density | 1.748 g/cm3 |
Reference Reading
1. Systematic evaluation and optimization of high-performance liquid chromatography separation of polyoxins
Zhidong Li, Qing Fu, Shiliang Li, Yu Jin, Xinmiao Liang J Sep Sci. 2020 Aug;43(15):3006-3016. doi: 10.1002/jssc.202000269. Epub 2020 Jul 12.
The chromatographic behavior of a kind of nucleoside peptides, polyoxins, was investigated in this study. Molecular simulation technique was used to elucidate the temperature-dependent peak sharpening of polyoxins. There was a relatively small energy barrier between the global minimum conformer and the local minimum conformer of polyoxin A and the high temperature helped to quickly cross the energy barrier and accelerate the conformational transformation for getting the global minimum, so that stationary phase could not identify these two conformations and presented a sharp peak. Two kinds of mixed-mode columns, strong cation exchange or strong anion exchange ligands bonded with C18 (C18SCX and C18SAX) were used to improve separation selectivity of four polyoxins (A, K, F, H). The electrostatic attraction was necessary to increase the retention to ensure that the alkyl chain can give better play to its hydrophobic effect. Therefore, four polyoxins were well separated on C18SCX at pH 2 and they were also well separated on C18SAX at pH 7. In the small-scale purification of polyoxins, the sample loading of the C18SCX was five times than that of the C18SAX and the purity of the collected four polyoxins was all over 90%.
2. Bioactivity-guided separation of antifungal compounds by preparative high-performance liquid chromatography
Zhidong Li, Zhuoshun Dai, Dasen Jiang, Yingping Dai, Yu Jin, Qing Fu, Xinmiao Liang J Sep Sci. 2021 Jun;44(12):2382-2390. doi: 10.1002/jssc.202100072. Epub 2021 May 12.
Bioactivity-guided chromatographic methods are of great significance for the isolation of the active compounds in complex samples. In this study, four anti-fungal compounds were located by activity screening and successfully isolated from a microbial fermentation sample by preparative high-performance liquid chromatography. Separation performance of columns including C18, positively charged C18, negatively charged C18 and C8 were firstly investigated. And it showed a better capacity of mixed-mode stationary phases for retention and separation. Therefore, the positively charged C18 column was used to separate the sample into several fractions, among which the active one was identified by the antifungal test. And then the active fraction was enriched and separated again by successively using the negatively charged C18 and C8 columns to obtain four compounds, which were identified as polyoxins A, K, F and H. With activity verification, four polyoxins were found to have good inhibitory effects against the three fungal plant diseases including rice sheath blight, tomato grey mould disease, and apple spot leaf disease.
3. Cross-genus inhibitory activity of polyoxins against aflatoxin production by Aspergillus parasiticus and fumonisin production by Fusarium fujikuroi
Tomoya Yoshinari, Maiko Watanabe, Yukiko Hara-Kudo FEMS Microbiol Lett. 2022 Jul 28;369(1):fnac048. doi: 10.1093/femsle/fnac048.
Co-exposure to aflatoxin and fumonisin is a health concern where corn is a staple food, and a method to prevent co-contamination of these mycotoxins in foods is urgently needed. Polyoxins are chitin synthase inhibitors produced by Streptomyces cacaoi var. asoensis. The aflatoxin production inhibitory activity of a commercially available polyoxin D and four polyoxins purified from polyoxin AL water-soluble powder, an agricultural chemical containing polyoxins, was tested. The five polyoxins dose-dependently inhibited aflatoxin production by Aspergillus parasiticus and the IC50 values of polyoxin A, B, D, K and L were 16, 74, 110, 9 and 280 µmol L-1, respectively. Polyoxins also inhibited fumonisin production by Fusarium fujikuroi, and the IC50 values of polyoxin B, D, K and L were 270, 42, 65 and 62 µmol L-1, respectively. Polyoxins repressed the transcription of genes encoding proteins required for aflatoxin biosynthesis in A. parasiticus and fumonisin biosynthesis in F. fujikuroi. Polyoxin K and D also inhibited conidiation in A. parasiticus and F. fujikuroi, respectively. These results suggest that a mixture of polyoxins may effectively prevent co-contamination of aflatoxin and fumonisin in foods.
Recommended Products
| BBF-00677 | 3-Amino-3-deoxy-D-glucose | Inquiry |
| BBF-01825 | Loganin | Inquiry |
| BBF-01829 | Deoxynojirimycin | Inquiry |
| BBF-02642 | Lactonamycin | Inquiry |
| BBF-00764 | Cerebroside C | Inquiry |
| BBF-01693 | Doxorubicin EP Impurity A (Daunorubicin) | Inquiry |
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 ╳
