title: Mechanistic model for the firefly luciferin regeneration in biomimetic conditions: a model for the in vivo process?
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.
authors.affiliation: Centro de Ciências Naturais e Humanas, Universidade Federal do ABC, Av. dos Estados 5001, Santo André/SP 09210-580, Brazil. luiz.ciscato@ufabc.edu.br.
authors.forename: Carla T
authors.initials: CT
authors.lastname: Salatino
authors.forename: Diêgo U
authors.initials: DU
authors.lastname: Melo
authors.forename: Ariane M
authors.initials: AM
authors.lastname: Yoshitake
authors.forename: Lucas S
authors.initials: LS
authors.lastname: Sgarbi
authors.forename: Paula
authors.initials: P
authors.lastname: Homem-de-Mello
authors.forename: Fernando H
authors.initials: FH
authors.lastname: Bartoloni
authors.forename: Luiz F M L
authors.initials: LFML
authors.lastname: Ciscato