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

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• 作者：Valentin N. Petushkov ; Aleks ; ra S. Tsarkova ; Maxim A. Dubinnyi ; Natalja S. Rodionova ; Simone M. Marques ; Joaquim C.G. Esteves da Silva ; Osamu Shimomura ; Ilia V. Yampolsky
• 关键词：Bioluminescence ; Enchytraeid ; Luciferin ; Total synthesis
• 刊名：Tetrahedron Letters
• 出版年：8 January, 2014
• 年：2014
• 卷：55
• 期：2
• 页码：460-462
• 全文大小：498 K

文摘

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.