Structural and electronic characterization of a Fridericia heliota luciferin-related derivative, based on quantum chemistry

• Type: Article in International Scientific Journal
• Date: 2014

Authors

Luis Pinto da Silva (Author) Other; Joaquim C G E Esteves da Silva (Author) FCUP

Journal

Title: Journal of Photochemistry and Photobiology A: Chemistry

Vol. 288

Pages: 46-54

ISSN: 1010-6030

Publisher: Elsevier

Indexing

ISI Web of Knowledge - 0 Citations

Scopus - 0 Citations

Scientific classification

FOS: Natural sciences > Chemical sciences

Other information

Authenticus ID: P-009-GNN

DOI: 10.1016/j.jphotochem.2014.05.005

Abstract (EN): CompX is a natural analog of the unknown luciferin of the bioluminescence earthworm Fridericia heliota. Given the difficulties of characterizing luciferin, the objective of this work was the quantum chemistry based structural and electronic characterization of CompX. A main feature of this molecule is a strong partially covalent O-H center dot center dot center dot O ionic bond, with sigma bonding character, present in all CompX species. Atomic charge transfers involving this interaction determine the relative stability of all species. Moreover, this interaction is involved in an excited state intramolecular proton transfer leading to a phototautomerism reaction. Thus, the large Stokes shift observed for CompX is attributed to an enol -> keto photoconversion.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 9