Polyoxorim
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| Category | Antifungal |
| Catalog number | BBF-05736 |
| CAS | 22976-86-9 |
| Molecular Weight | 521.39 |
| Molecular Formula | C17H23N5O14 |
| Purity | ≥96% |
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Description
Polyoxorim is a member of the class of polyoxins that is isolated from the soil organism Streptomyces cacaoi var. asoensis. Polyoxorim exhibits fungicidal properties and may be used on rice, industrial grounds, golf courses and parks. It has a role as an EC 2.4.1.16 (chitin synthase) inhibitor and an antifungal agrochemical. It is a polyoxin and an antibiotic fungicide.
Specification
| Related CAS | 146659-78-1 (zinc salt) |
| Synonyms | 5-[[2-Amino-5-O-(aminocarbonyl)-2-deoxy-L-xylonoyl]amino]-1-(5-carboxy-3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl)-1,5-dideoxy-β-D-allofuranuronic acid; Polyoxin D; 1-{5-[{[2-amino-5-(carbamoyloxy)-3,4-dihydroxypentanoyl]amino}(carboxy)methyl]-3,4-dihydroxytetrahydrofuran-2-yl}-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid(non-preferred name); Polyoxin D, Streptomyces cacaoi var asoensis |
| Storage | Store at RT |
| IUPAC Name | 1-[(2R,3R,4S,5R)-5-[(S)-[[(2S,3S,4S)-2-amino-5-carbamoyloxy-3,4-dihydroxypentanoyl]amino]-carboxymethyl]-3,4-dihydroxyoxolan-2-yl]-2,4-dioxopyrimidine-5-carboxylic acid |
| Canonical SMILES | C1=C(C(=O)NC(=O)N1C2C(C(C(O2)C(C(=O)O)NC(=O)C(C(C(COC(=O)N)O)O)N)O)O)C(=O)O |
| InChI | InChI=1S/C17H23N5O14/c18-5(7(24)4(23)2-35-16(19)33)12(28)20-6(15(31)32)10-8(25)9(26)13(36-10)22-1-3(14(29)30)11(27)21-17(22)34/h1,4-10,13,23-26H,2,18H2,(H2,19,33)(H,20,28)(H,29,30)(H,31,32)(H,21,27,34)/t4-,5-,6-,7+,8-,9+,10+,13+/m0/s1 |
| InChI Key | JPFWJDMDPLEUBD-ITJAGOAWSA-N |
Properties
| Appearance | White solid |
| Antibiotic Activity Spectrum | Fungi |
| Melting Point | 173-175°C (dec.) |
| Density | 1.864±0.06 g/cm3 (Predicted) |
| Solubility | Soluble in Aqueous Buffers, Water |
Reference Reading
1. Can a chitin-synthesis-inhibiting turfgrass fungicide enhance black cutworm susceptibility to a baculovirus?
Daniel A Potter, Andrea J Bixby-Brosi Pest Manag Sci . 2012 Mar;68(3):324-9. doi: 10.1002/ps.2252.
Background:Developmental resistance, i.e. reduced virulence and speed of kill of late instars, is a limiting factor in the use of baculoviruses for caterpillar control. Agrotis ipsilon multicapsid nucleopolyhedrovirus (AgipMNPV) is highly infective to young black cutworms, Agrotis ipsilon, but too slow-acting against late instars for effective curative control on golf courses or sports fields. Chitin-synthesis-inhibiting fungicides containing the active ingredient polyoxin-d are used to control fungal diseases in turfgrass, and similar compounds have been shown in the laboratory to synergize baculoviruses by disrupting peritrophic membrane function. This study tested whether applying the virus together with such a fungicide can synergize AgipMNPV activity against A. ipsilon in turfgrass.Results:The addition of a chitin synthesis inhibitor failed to increase AgipMNPV infectivity to A. ipsilon in the field. Rather, delayed and slightly reduced mortality from viral infection was seen when larvae fed on fungicide/virus-treated grasses as opposed to virus-only treatments. Choice tests revealed the fungicide residues to be a mild feeding deterrent.Conclusion:Because polyoxin-d does not deactivate AgipMNPV, the two substances are compatible. However, combination applications of polyoxin-d and Agip MNPV on turfgrass might interfere with larval ingestion of a lethal virus dose, resulting in prolonged larval feeding in the field.
2. Characterization of chitin synthase from Botrytis cinerea
R J Milling, S G Foster, D J Adams, B E Causier Microbiology (Reading) . 1994 Sep;140 ( Pt 9):2199-205. doi: 10.1099/13500872-140-9-2199.
Chitin synthase in a microsomal preparation from Botrytis cinerea had an apparent Km for UDP-N-acetylglucosamine of 2.0 mM while nikkomycin Z and polyoxin D inhibited enzyme activity competitively with apparent Ki values of approximately 0.1 microM and 6 microM respectively. The organophosphorus fungicide edifenphos was a non-competitive inhibitor (Ki(app) 54 microM). Preincubation of microsomes for 2 h at 25 degrees C resulted in a maximum twofold stimulation of chitin synthase activity while preincubation with trypsin (25 micrograms ml-1) or cytosol (350 micrograms cytosolic protein ml-1) for 10 min at 25 degrees C resulted in approximately fourfold and 20-fold increases in chitin synthase activity, respectively. A range of protease inhibitors reduced the degree of activation of microsomal chitin synthase by cytosol. Most potent were phenylmethanesulphonyl fluoride and chymostatin; these compounds completely inhibited activation of enzyme activity. Two fragments (approx. 600 bp; CHS1 and CHS2) were amplified from B. cinerea genomic DNA using degenerate PCR primers based on regions of complete amino acid homology between previously published chitin synthase gene sequences. When the DNA and predicted amino acid sequences of CHS1 were used to probe computer databases for related sequences, B. cinerea CHS1 was found to be most similar to CHS1 from Neurospora crassa.
3. Inhibition of chitin synthases and antifungal activities by 2'-benzoyloxycinnamaldehyde from Pleuropterus ciliinervis and its derivatives
Bong Sik Yun, Eui Il Hwang, Tae Hoon Kang, Sung Uk Kim, Byoung Mog Kwon, Ki Duk Park, Chul Soo Shin Biol Pharm Bull . 2007 Mar;30(3):598-602. doi: 10.1248/bpb.30.598.
In the course of search for potent chitin synthase inhibitors from natural resources, a novel chitin synthases inhibitor, 2'-benzoyloxycinnamaldehyde (2'-BCA) (I), was isolated from the aerial parts of Pleuropterus ciliinervis NAKAI. 2'-BCA inhibited chitin synthase 1 and 2 of Saccharomyces cerevisiae with the IC50s of 54.9 and 70.8 microg/ml, respectively, whereas it exhibited no inhibitory activity for chitin synthase 3 up to 280 microg/ml. Its derivatives, 2'-chloro- (V) and 2(-bromo-cinnamaldehyde (VI), each showed 1.9 and 2.7-fold stronger inhibitory activities than 2'-BCA, with the IC50s of 37.2 and 26.6 microg/ml, respectively. Especially, the IC50 of compound VI against chitin synthase 2 represented 1.7-fold more potent inhibitory activity than polyoxin D, a well-known chitin synthase inhibitor. Furthermore, compounds V and VI showed potent antifungal activities against various fungi including human pathogenic fungi, with a particularly strong inhibitory activity against Cryptococcus neoformans (MIC = 16 microg/ml). Although the chemical synthesis of this compound has been reported, the present study is the first report to describe the isolation of 2'-BCA from natural resources and chitin synthases inhibitory activities of its derivatives. These results suggested that 2'-BCA and its derivatives can potentially serve as useful lead compounds for development of antifungal agents.
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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 ╳
