CompX, a luciferin-related tyrosine derivative from the bioluminescent earthworm Fridericia heliota. Structure elucidation and total synthesis

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

Authors

petushkov, vn (Author) Other; tsarkova, as (Author) Other; dubinnyi, ma (Author) Other; rodionova, ns (Author) Other; marques, sm (Author) Other; esteves da silva, jcg (Author) FCUP; shimomura, o (Author) Other; yampolsky, iv (Author) Other

Journal

Title: Tetrahedron Letters

Vol. 55

Pages: 460-462

ISSN: 0040-4039

Publisher: Elsevier

Indexing

ISI Web of Knowledge - 10 Citations

Scopus - 10 Citations

Scientific classification

FOS: Natural sciences > Chemical sciences

Other information

Authenticus ID: P-008-K0P

DOI: 10.1016/j.tetlet.2013.11.064

Abstract (EN): A luciferin analog, CompX, was isolated from the extracts of the bioluminescent earthworm Fridericia heliota. Its structure was determined as (Z)-5-(2-carboxy-2-methoxyvinyl)-2-hydroxybenzoic acid by spectroscopic data analysis and was confirmed by total synthesis. The (Z)-configuration of the double bond was established by comparing the ROESY spectra of CompX with those of its synthetic (E)-isomer. CompX represents a tyrosine analog, not previously found in natural sources, and is probably derived from tyrosine by deamination, O-methylation of the resulting alpha-keto acid, and carboxylation at the aromatic core.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 3