Тип публикации: статья из журнала
Год издания: 2014
Идентификатор DOI: 10.1016/j.tetlet.2013.11.064
Ключевые слова: Bioluminescence, Enchytraeid, Luciferin, Total synthesis, 2 oxoacid, 5 (2 carboxy 2 methoxyvinyl) 2 hydroxybenzoic acid, CompX, hydroxybenzoic acid derivative, tyrosine derivative, unclassified drug, oxoacid, aqueous solution, article, carboxylation, chemical structure, chromatography, data analysis, deamination, drug structure, drug synthesis, earthworm, Fridericia heliota, heteronuclear multiple bond correlation, Horner Wadsworth Emmons reaction, methylation, nonhuman, proton nuclear magnetic resonance, spectroscopy, isomer, nuclear magnetic resonance spectroscopy, pH, structure analysis, ultraviolet radiation, Enchytraeidae
Аннотация: 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 compariПоказать полностьюng 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. (C) 2013 Elsevier Ltd. All rights reserved.
Журнал: TETRAHEDRON LETTERS
Выпуск журнала: Vol. 55, Is. 2
Номера страниц: 460-462
ISSN журнала: 00404039
Место издания: OXFORD
Издатель: PERGAMON-ELSEVIER SCIENCE LTD