38481-04-8Relevant academic research and scientific papers
Second bioluminescence-activating component in the luminous fungus Mycena chlorophos
Teranishi, Katsunori
, p. 182 - 189 (2017)
Mycena chlorophos is an oxygen-dependent bioluminescent fungus. The mechanisms underlying its light emission are unknown. A component that increased the bioluminescence intensity of the immature living gills of M. chlorophos was isolated from mature M. chlorophos gills and chemically characterized. The bioluminescence-activating component was found to be trans-3,4-dihydroxycinnamic acid and its bioluminescence activation was highly structure-specific. 13C- and 18O-labelling studies using the immature living gills showed that trans-3,4-dihydroxycinnamic acid was synthesized from trans-4-hydroxycinnamic acid in the gills by hydroxylation with molecular oxygen as well as by the general metabolism, and trans-3,4-dihydroxycinnamic acid did not produce hispidin (detection-limit concentration: 10 pmol/1 g wet gill). Addition of 0.01 mM hispidin to the immature living gills generated no bioluminescence activation. These results suggested that the prompt bioluminescence activation resulting from addition of trans-3,4-dihydroxycinnamic acid could not be attributed to the generation of hispidin. Copyright
Cis-trans isomerization of a cyclopropyl radical trap catalyzed by extradiol catechol dioxygenases: Evidence for a semiquinone intermediate
Spence, Emma L.,Langley, G. John,Bugg, Timothy D. H.
, p. 8336 - 8343 (2007/10/03)
Substrate analogues cis- and trans-2-(2,3-dihydroxyphenyl)cyclopropane-1-carboxylic acid were synthesized as probes for a semiquinone radical intermediate in the (2,3-dihydroxyphenyl)propionate 1,2-dioxygenase reaction. These analogues were found to be substrates for oxidative cleavage by extradiol dioxygenases from Escherichia coli and Alcaligenes eutrophus. The stereochemistry of the ring fission products was analyzed by conversion to cyclopropane-1,2-dicarboxylic acids using the ensuing hydrolase enzyme MhpC, followed by GCMS analysis. This analysis revealed 85-94% trans product and 6-15% cis products, implying that cis/trans isomerization of the cyclopropyl ring substituents had taken place during the enzymatic conversion. These results are consistent with a reversible opening of the cyclopropyl ring, and hence consistent with the intermediacy of a semiquinone radical intermediate in the extradiol catechol dioxygenase reaction.
PHASE TRANSFER CATALYSED WITTIG-HORNER SYNTHESIS PREPARATION OF HYDROXYCINNAMIC ESTERS FROM ORTHO HYDROXY AROMATIC ALDEHYDES OBTENTION OF HYDROXYCINNAMIC ACIDS
Dupin, J. F. E.,Chenault, J.
, p. 581 - 586 (2007/10/02)
Reaction between (carbethoxymethyl)-triphenylphosphonium bromide and ortho hydroxyaromatic aldehydes gives hydroxycinnamic esters in a liquid-solid two phases system (potassium carbonate-methanol) with a good yield.
