Abstract
Abstract 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.
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