A Novel Type of Luciferin from the Siberian Luminous Earthworm Fridericia heliota: Structure Elucidation by Spectral Studies and Total Synthesis

Описание

Тип публикации: статья из журнала

Год издания: 2014

Идентификатор DOI: 10.1002/anie.201400529

Ключевые слова: bioluminescence, luciferin, natural products, NMR spectroscopy, total synthesis, bioluminescence, luciferin, natural products, NMR spectroscopy, total synthesis, Bioluminescence, Biosynthesis, Fluorescence, Isomers, Nuclear magnetic resonance spectroscopy, Phosphorescence, Spectroscopic analysis, Aminobutyric acids, Bioluminescent systems, Isomeric structures, luciferin, Mechanism of action, Natural products, Structure elucidation, Total synthesis, Amino acids, adenosine triphosphate, luminescent agent, peptide, animal, chemistry, isomerism, luminescence, metabolism, Oligochaeta, Russian Federation, synthesis, Adenosine Triphosphate, Animals, Isomerism, Luminescent Agents, Luminescent Measurements, Oligochaeta, Peptides, Siberia

Аннотация: The structure elucidation and synthesis of the luciferin from the recently discovered luminous earthworm Fridericia heliota is reported. This luciferin is a key component of a novel ATP-dependent bioluminescence system. UV, fluorescence, NMR, and HRMS spectroscopy studies were performed on 0.005 mg of the isolated substance and revПоказать полностьюealed four isomeric structures that conform to spectral data. These isomers were chemically synthesized and one of them was found to produce light when reacted with a protein extract from F. heliota. The novel luciferin was found to have an unusual extensively modified peptidic nature, thus implying an unprecedented mechanism of action.

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Издание

Журнал: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Выпуск журнала: Vol. 53, Is. 22

Номера страниц: 5566-5568

ISSN журнала: 14337851

Место издания: WEINHEIM

Издатель: WILEY-V C H VERLAG GMBH

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 660036, Russia)
  • Dubinnyi Maxim A. (Russian Acad Sci, Inst Bioorgan Chem, Moscow 117997, Russia)
  • Tsarkova Aleksandra S. (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 660036, Russia)
  • Baranov Mikhail S. (Russian Acad Sci, Inst Bioorgan Chem, Moscow 117997, Russia)
  • Kublitski Vadim S. (Russian Acad Sci, Inst Bioorgan Chem, Moscow 117997, Russia)
  • Shimomura Osamu (Siberian Fed Univ, Inst Fundamental Biol & Biotechnol, Lab Bioluminescent Biotechnol, Krasnoyarsk 660041, Russia; Marine Biol Lab, Woods Hole, MA 02543 USA)
  • Yampolsky Ilia V. (Russian Acad Sci, Inst Bioorgan Chem, Moscow 117997, Russia)

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