AK-toxin I
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| Category | Mycotoxins |
| Catalog number | BBF-00396 |
| CAS | 85146-09-4 |
| Molecular Weight | 413.46 |
| Molecular Formula | C23H27NO6 |
| Purity | 95% |
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Description
It is produced by the strain of Alternaria kikuchiana AS-1223. It's a plant toxin (especially for pear trees).
Specification
| Synonyms | CTK3E8898; (2E,4E,6E)-8-(2-acetamido-3-phenyl-butanoyl)oxy-8-(2-methyloxiran-2-yl)octa-2,4,6-trienoic Acid |
| IUPAC Name | 8-(2-acetamido-3-phenylbutanoyl)oxy-8-(2-methyloxiran-2-yl)octa-2,4,6-trienoic acid |
| Canonical SMILES | CC(C1=CC=CC=C1)C(C(=O)OC(C=CC=CC=CC(=O)O)C2(CO2)C)NC(=O)C |
| InChI | InChI=1S/C23H27NO6/c1-16(18-11-7-6-8-12-18)21(24-17(2)25)22(28)30-19(23(3)15-29-23)13-9-4-5-10-14-20(26)27/h4-14,16,19,21H,15H2,1-3H3,(H,24,25)(H,26,27) |
| InChI Key | HGSOUJPIFSDBKJ-UHFFFAOYSA-N |
Properties
| Appearance | Crystal |
| Boiling Point | 656.0 °C at 760 mmHg |
| Melting Point | 168 °C (dec.) |
| Density | 1.205 g/cm3 |
| Solubility | Soluble in Methanol |
Reference Reading
1. Host-selective toxins and avirulence determinants: what's in a name?
Thomas J Wolpert, Larry D Dunkle, Lynda M Ciuffetti Annu Rev Phytopathol. 2002;40:251-85. doi: 10.1146/annurev.phyto.40.011402.114210. Epub 2002 Feb 20.
Host-selective toxins, a group of structurally complex and chemically diverse metabolites produced by plant pathogenic strains of certain fungal species, function as essential determinants of pathogenicity or virulence. Investigations into the molecular and biochemical responses to these disease determinants reveal responses typically associated with host defense and incompatibility induced by avirulence determinants. The characteristic responses that unify these disparate disease phenotypes are numerous, yet the evidence implicating a causal relationship of these responses, whether induced by host-selective toxins or avirulence factors, in determining the consequences of the host-pathogen interaction is equivocal. This review summarizes some examples of the action of host-selective toxins to illustrate the similarity in responses with those to avirulence determinants.
2. Synthesis of the Methyl Ester of Tritium-labeled AK-toxin I, a Host-specific Toxin Produced by Alternaria alternata Japanese Pear Pathotype
M Okada, H Miyagawa, T Ueno Biosci Biotechnol Biochem. 1999;63(7):1253-60. doi: 10.1271/bbb.63.1253.
AK-toxin I, a host-specific toxin to Japanese pear (Pyrus serotina), was synthesized as its methyl ester from three precursor fragments: conjugated diene-carboxylic acid, chiral epoxyalcohol and β-methylphenylalanine. The epoxyalcohol fragment was derived from D-fructose, in which effective homologation of the hemiacetal carbon to alkyne by using dimethyl 1-diazo-2-oxopropylphosphonate was the key reaction. The diene-carboxylic acid fragment was prepared by repeated Wittig reactions, and was combined with the epoxyalcohol fragment by the Stille reaction. Esterification of the combined product with the stereochemically-pure β-methylphenylalanine fragment afforded the target compound. This method was used to prepare the methyl ester of tritium-labeled AK-toxin I with a specific radioactivity of 213 GBq/mmol.
3. Binding affinity of the methyl ester of AK-toxin I to membrane fractions from Japanese pear leaves
M Okada, H Miyagawa, Y Nakagawa, T Ueno Biosci Biotechnol Biochem. 2000 Nov;64(11):2517-21. doi: 10.1271/bbb.64.2517.
The binding site of AK-toxin, a host-specific toxin against Japanese pear, was searched for in the membrane fractions of the pear leaves, using 3H-labeled AK-toxin I methyl ester. Binding activity, which was displaceable by the unlabeled ligand, was observed for microsomal fraction from a toxin-susceptible cultivar, Nijisseiki. However, the binding was also observed for those from toxin-resistant cultivars, Kosui and Hosui. Detection of the specific binding failed for the plasma membrane fraction which was prepared from microsomal fraction of the toxin-susceptible cultivar by aqueous two-phase separation, and the hitherto presumed model of the AK-toxin receptor in the plasma membrane could not be verified.
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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 ╳
