38818-51-8

Usage

InChI:InChI=1/C19H26O6/c1-11-5-6-18(9-22-12(2)20)15(7-11)25-16-14(24-13(3)21)8-17(18,4)19(16)10-23-19/h7,14-16H,5-6,8-10H2,1-4H3/t14-,15-,16-,17-,18-,19?/m1/s1

Upstream product

• 108-24-7 acetic anhydride 
• 119649-07-9 3α-acetoxy-10β-bromo-9α,15;12,13-diepoxytrichothecane 
• 28624-60-4 trichodiene 
• 67-64-1 acetone 
• 80513-95-7 (4aR,8aR)-4a-Hydroxymethyl-4,7-dimethyl-4a,5,6,8a-tetrahydro-4H-chromen-3-one 
• 2270-40-8 4,15-diacetoxyscirpenol 
• 119649-01-3 10β-bromo-9α,15;12,13-diepoxytrichothecan-3-one 
• 123618-93-9 15-Deacetylcalonectrin 
• 72-89-9 S-acetyl coenzyme A 
• 119649-00-2 10β-bromo-3α,4β-bismethysulphonyloxy-9α,15;12,13-diepoxytrichothecane 
• 2270-41-9 scirpentriol 
• 119662-81-6 C₁₅H₂₁BrO₅ 
• 119649-02-4 10β-bromo-3α-hydroxy-9α,15;12,13-diepoxytrichothecane 
• 80484-06-6 [(4R,4aR,8aR)-4a-(tert-Butyl-dimethyl-silanyloxymethyl)-4,7-dimethyl-3-oxo-3,4,4a,5,6,8a-hexahydro-2H-chromen-4-yl]-acetic acid methyl ester 

Downstream Products

• 81452-35-9 C₁₅H₂₀O₅ 

Relevant academic research and scientific papers

4-O-acetylation and 3-O-acetylation of trichothecenes by trichothecene 15-O-acetyltransferase encoded by Fusarium Tri3

In the biosynthesis of Fusarium trichothecenes, the C-3 hydroxyl group of isotrichodermol must be acetylated by TRI101 for subsequent pathway genes to function. Despite the importance of this 3-O-acetylation step in biosynthesis, Tri101 is both physically and evolutionarily unrelated to other Tri genes in the trichothecene gene cluster. To gain insight into the evolutionary history of the cluster, we purified recombinant TRI3 (rTRI3), one of the two cluster gene-encoded trichothecene O-acetyltransferases, and examined to determine whether this 15-O-acetyltransferase can add an acetyl to the C-3 hydroxyl group of isotrichodermol. When a high concentration of rTRI3 was used in the assay (final concentration, 50μM), we observed 3-O-acetylation activity against isotrichodermol that was more than 105 times less efficient than the known 15-O-acetylation activity against 15-deacetylcalonectrin. The rTRI3 protein also exhibited 4-O-acetylation activity when nivalenol was used as a substrate; in addition to 15-acetylnivalenol, di-acetylated derivatives, 4,15- diacetylnivalenol, and, to a lesser extent, 3,15-diacetylnivalenol, were also detected at high enzyme concentrations. The significance of the trace trichothecene 3-O-acetyltransferase activity detected in rTRI3 is discussed in relation to the evolution of the trichothecene gene cluster.

Trichothecene mycotoxin interconversions: Partial syntheses of calonectrin and deoxynivalenol, and of a trichothecene epi-epoxide, 3α,4β,15-triacetoxy-12,13-epi-epoxytrichothec-9-ene

The partial syntheses of two trichothecenes, calonectrin (4β,15-diacetoxy-12,13-epoxytrichothec-9-ene) and deoxynivalenol (3α,7α,15-trihydroxy-12,13-epoxytrichothec-9-ene), from a readily available trichothecene, anguidine (4β,15-diacetoxy-3α-hydroxy-12,13-epoxytrichothec-9-ene) are described. In addition, and in order to provide further insight into the mode of action of the trichothecene mycotoxins, 3α,4β,15-tricetoxy-12,13-epi-epoxytrichothec-9-ene, of the first semisynthetic trichothecene epi-epoxides, has been prepared and its X-ray crystal structure determined. In significant contrast to its natural isomer, epi-epoxide proved to be biologically inactive.

PARTIAL SYNTHESES OF THE TRICHOTHECENE MYCOTOXINS, CALONECTRIN AND DEOXYNIVALENOL

The partial syntheses of two trichothecenes, calonectrin (1) and deoxynivalenol (2), from a readily available derivative of the trichothecene, anguidine, are described.The methodology used should be applicable to the provision of other less abundant trichothecenes.