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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Mechanistic model for the firefly luciferin regeneration in biomimetic conditions: a model for the in vivo process?

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Salatino, Carla T. ; Melo, Diego U. ; Yoshitake, Ariane M. ; Sgarbi, Lucas S. ; Homem-de-Mello, Paula ; Bartoloni, Fernando H. ; Ciscato, Luiz F. M. L.
Total Authors: 7
Document type: Journal article
Source: ORGANIC & BIOMOLECULAR CHEMISTRY; v. 15, n. 16, p. 3479-3484, APR 28 2017.
Web of Science Citations: 2

The emission of light by fireflies involves the enzymatic oxidation of firefly luciferin and ends up in the formation of 2-cyano-6-hydroxybenzothiazole, and this is recycled back to luciferin by condensation with cysteine. In this work, we suggest a mechanism for this transformation that operates under mild conditions that are similar to in vivo environments (i.e. biomimetic); the rate-determining step consists of an intermolecular nucleophilic attack from the cysteine thiolate on the nitrile, catalysed by a specific base, followed by a complex sequence of intramolecular reactions which are highly dependent on the medium pH. (AU)

FAPESP's process: 12/02428-5 - Cyclic organic peroxides: synthesis and mechanism of reduction
Grantee:Luiz Francisco Monteiro Leite Ciscato
Support type: Regular Research Grants
FAPESP's process: 12/13807-7 - New tools for the study of electron transfer reactions in PS II model systems
Grantee:Fernando Heering Bartoloni
Support type: Regular Research Grants