AAL Toxin TA1
AAL-toxins TA 1 and TA 2 are host-specific toxins (HST) produced by Altemaria altemata f. sp. lycopersici, a causal fungus of tomato stem canker.
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Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to
24 months(2-8C).
Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour.
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The Absolute Configuration of Host-specific Toxin, AAL-toxin TA and Its Synthetic Study[Reference:
WebLink]
AAL Toxin TA1(1)and AALtoxin TA2(2)are host-specific toxins (HST) produced by Altemaria altemata f. sp. lycopersici, a causal fungus of tomato stem canker. For understanding the mechanism of the host-specificity of AAL-toxins in molecular level, the elucidation of the stereostructure and synthetic studies are essential.
METHODS AND RESULTS:
In order to determine the absolute configuration, 1 and 2 were degraded to 2-methylbutanol, 3-methylnonan-1,9-diol and N-protected 4-amino-butan-1,3-diol, which were further converted to (R)-MTPA esters, These esters were correlated with synthetic samples by comparison of their 500MHz ^1H-NMR spectra. The remaining stereocenters were determined by the comparison of ^1H-NMR spectra of 6a and 6c derived from 1 and 2 with those of synthetic model compounds. These data concluded that AAL-toxins possess 2S, 4S, 5S, 11S, 13S, 14R and 15R configurations. To the syntheses of two vicinal anti-diol moieties in key intermediates of AAL-toxins, asymmetric dihydroxylation has been applied.
CONCLUSIONS:
The strategy allowed efficient construction of left- and right segments of AAL-toxin main chain. Enzymatic resolution of benzylsuccinate ester provided both enantiomers (R)-39 and (S)-40 which were converted to the corresponding tricarballylic acids. Effective couplings of each segment were also investigated.
