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

Описание

Тип публикации: статья из журнала

Год издания: 2014

Идентификатор DOI: 10.1016/j.tetlet.2013.11.064

Ключевые слова: Bioluminescence, Enchytraeid, Luciferin, Total synthesis, Bioluminescence, Enchytraeid, Luciferin, Total synthesis, 2 oxoacid, 5 (2 carboxy 2 methoxyvinyl) 2 hydroxybenzoic acid, CompX, hydroxybenzoic acid derivative, luciferin, tyrosine derivative, unclassified drug, 5 (2 carboxy 2 methoxyvinyl) 2 hydroxybenzoic acid, luciferin, oxoacid, tyrosine derivative, aqueous solution, article, bioluminescence, 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, Article, isomer, nuclear magnetic resonance spectroscopy, pH, structure analysis, ultraviolet radiation, Enchytraeidae, Fridericia heliota, Enchytraeidae, Fridericia heliota

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.

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Издание

Журнал: TETRAHEDRON LETTERS

Выпуск журнала: Vol. 55, Is. 2

Номера страниц: 460-462

ISSN журнала: 00404039

Место издания: OXFORD

Издатель: PERGAMON-ELSEVIER SCIENCE LTD

Авторы

  • Petushkov Valentin N. (Siberian Fed Univ, Inst Fundamental Biol & Biotechnol, Lab Bioluminescent Biotechnol, Krasnoyarsk 660041, Russia; Russian Acad Sci, Siberian Branch, Inst Biophys, Lab Photobiol, Krasnoyarsk 660035, Russia)
  • Tsarkova Aleksandra S. (Russian Acad Sci, Inst Bioorgan Chem, Moscow 117997, Russia)
  • Dubinnyi Maxim A. (Russian Acad Sci, Inst Bioorgan Chem, Moscow 117997, Russia)
  • Rodionova Natalja S. (Siberian Fed Univ, Inst Fundamental Biol & Biotechnol, Lab Bioluminescent Biotechnol, Krasnoyarsk 660041, Russia; Russian Acad Sci, Siberian Branch, Inst Biophys, Lab Photobiol, Krasnoyarsk 660035, Russia)
  • Marques Simone M. (Univ Porto, Fac Sci, Dept Chem & Biochem, Chem Res Ctr Univ Porto CIQ UP, P-4169007 Oporto, Portugal)
  • Esteves da Silva Joaquim C. G. (Univ Porto, Fac Sci, Dept Chem & Biochem, Chem Res Ctr Univ Porto CIQ UP, P-4169007 Oporto, Portugal)
  • Shimomura Osamu (Siberian Fed Univ, Inst Fundamental Biol & Biotechnol, Lab Bioluminescent Biotechnol, Krasnoyarsk 660041, Russia)
  • Yampolsky Ilia V. (Russian Acad Sci, Inst Bioorgan Chem, Moscow 117997, Russia)

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