| Full text | |
| Author(s): |
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 |
| Abstract | |
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 Opportunities: | 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 Opportunities: | Regular Research Grants |