Ca2+-regulated photoproteins of ctenophores lose bioluminescence
activity when exposed to visible light. Little is known about the
chemical nature of chromophore photoinactivation. Using a total synthesis
strategy, we have established the structures of two unusual coelenterazine
products, isolated from recombinant berovin of the ctenophore Beroe abyssicola, which are Z/E isomers. We propose that during light irradiation, these derivatives
are formed from 2-hydroperoxycoelenterazine via the intermediate 8a-peroxide
by a mechanism reminiscent of that previously described for the auto-oxidation
of green-fluorescent-protein-like chromophores.
We report the first total synthesis of racemic Odontosyllis
undecimdonta luciferin, a thieno[3,2-f]thiochromene
tricarboxylate comprising a 6-6-5-fused tricyclic skeleton with three
sulfur atoms in different electronic states. The key transformation
is based on tandem condensation of bifunctional thiol-phosphonate,
obtained from dimethyl acetylene dicarboxylate, with benzothiophene-6,7-quinone.
The presented convergent approach provides the synthesis of the target
compound with a previously unreported fused heterocyclic core in 11
steps, thus allowing for unambiguous confirmation of the chemical
structure of Odontosyllis luciferin by 2D-NMR spectroscopy.
Biochemistry of bioluminescence of the marine parchment tubeworm Chaetopterus has been in research focus for over a century; however, the results obtained by various groups contradict each other. Here, we report the isolation and structural elucidation of three compounds from Chaetomorpha linum algae, which demonstrate bioluminescence activity with Chaetopterus luciferase in the presence of Fe2+ ions. These compounds are derivatives of polyunsaturated fatty acid peroxides. We have also obtained their structural analogues and demonstrated their activity in the bioluminescence reaction, thus confirming the broad substrate specificity of the luciferase.
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