39484-07-6Relevant academic research and scientific papers
2-S-cysteinylhydroquinone is an intermediate for the firefly luciferin biosynthesis that occurs in the pupal stage of the Japanese firefly, Luciola lateralis
Kanie, Shusei,Nakai, Ryosuke,Ojika, Makoto,Oba, Yuichi
, p. 223 - 229 (2018)
Firefly luciferin is a natural product that is well-known to function as the substrate of the bioluminescence reaction in luminous beetles. However, the details of the biosynthetic system are still unclear. In this study, we showed by LC-MS/MS analysis that stable isotope-labeled 2-S-cysteinylhydroquinone was incorporated into firefly luciferin in living firefly specimens. Comparison of the incorporation efficiency among the developmental stages suggested that firefly luciferin is biosynthesized predominantly in the pupal stage. We also accomplished the in vitro biosynthesis of firefly luciferin using 2-S-cysteinylhydroquinone and the crude buffer extract of firefly pupae, suggesting the presence of a biosynthetic enzyme in the pupal extract.
THE REACTION OF CYSTEINE WITH 1,4-BENZOQUINONE: A REVISION.
Crescenzi, O.,Prota, G.,Schultz, T.,Wolfram, L.J.
, p. 6447 - 6450 (2007/10/02)
Under carefully controlled conditions, the reaction of L-cysteine with 1,4-benzoquinone leads to a mixture of 1,4-benzothiazine oligomers, arising by decarboxylation and subsequent polymerization of the cyclic quinonimine 1, previously reported as the reaction product.When the reaction was stopped in the early stages by addition of sodium borohydride, work up of the mixture gave, besides the reduced dimer 11, the dihydrobenzothiazine 10, consistent with the intermediacy of the 3-unsubstituted benzothiazine 5.
