Title of article
CompX, a luciferin-related tyrosine derivative from the bioluminescent earthworm Fridericia heliota. Structure elucidation and total synthesis
Author/Authors
Petushkov، نويسنده , , Valentin N. and Tsarkova، نويسنده , , Aleksandra S. and Dubinnyi، نويسنده , , Maxim A. and Rodionova، نويسنده , , Natalja S. and Marques، نويسنده , , Simone M. and Esteves da Silva، نويسنده , , Joaquim C.G. and Shimomura، نويسنده , , Osamu and Yampolsky، نويسنده , , Ilia V.، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2014
Pages
3
From page
460
To page
462
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.
Keywords
Enchytraeid , luciferin , total synthesis , Bioluminescence
Journal title
Tetrahedron Letters
Serial Year
2014
Journal title
Tetrahedron Letters
Record number
1887618
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