F-19-dehydrocoelenterazine as probe to investigate the active site of symplectin

Fluorinated dehydrocoelenterazines (F-DCTs) were synthesized to study molecular mechanisms of symplectin; a photoprotein of luminous squid Symplectoteuthis oualaniensis L. F-DCTs reacted with dithiothreitol and glutathione under neutral conditions to give the stable chromophores as symplectin model....

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Bibliographic Details
Published inTetrahedron Vol. 58; no. 11; pp. 2117 - 2126
Main Authors Isobe, M, Fujii, T, Kuse, M, Miyamoto, K, Koga, K
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 11.03.2002
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
COELENTERAZINE
symplectin
C-13-DEHYDROCOELENTERAZINE
dehydrocoelenterazine
bioluminescence
ANALOGS
PHOTOPROTEIN AEQUORIN
MODEL
PHOTOOXYGENATION
LOW-TEMPERATURE
fluorine
LUMINOUS SQUID
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Summary:Fluorinated dehydrocoelenterazines (F-DCTs) were synthesized to study molecular mechanisms of symplectin; a photoprotein of luminous squid Symplectoteuthis oualaniensis L. F-DCTs reacted with dithiothreitol and glutathione under neutral conditions to give the stable chromophores as symplectin model. Reconstructed symplectin was also obtained by addition of F-DCTs into apo-symplectin, and showed bioluminescence to emit 50-65% amount of light as natural symplectin. The structure of the chromophores was determined by F-19 NMR, Q-TOF-MS, and MS/MS analyses. Sequencing of the chromopeptides of symplectin models prepared from F-DCTs and thiol compounds was accomplished by ESI-Q-TOF-MS/MS analysis. (C) 2002 Elsevier Science Ltd. All rights reserved.
ISSN:0040-4020
DOI:10.1016/S0040-4020(02)00100-X