Synthesis of 13C-dehydrocoelenterazine and model studies on Symplectoteuthis squid bioluminescence

被引：24

作者：

Isobe, M ^{[1
]}

Kuse, M ^{[1
]}

Yasuda, Y ^{[1
]}

Takahashi, H ^{[1
]}

机构：

[1] Nagoya Univ, Sch Bioagr Sci, Organ Chem Lab, Nagoya, Aichi 4648601, Japan

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1998年 / 8卷 / 20期

关键词：

D O I：

10.1016/S0960-894X(98)00525-3

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

In the photoprotein of an Okinawan squid bioluminescence of Symplectoteuthis oualaniensis L a dehydrocoelenterazine has been assigned as a chromophoric precursor to its apoprotein. To prove this mechanism, we have established new synthetic route to ca. 100 %C-13 incorporated dehydrocoelenterazine and coelenterazine at the neighboring carbon of the 2-position of 2,3-dihydroimidazo-[1,2a]-pyrazinone skeleton. This C-13 enriched dehydrocoelenterazine readily converted in equilibrium between its adduct forms as a diastereomixture with glutathione (GSH) or dithiothreitol (DTT) compounds having sulfhydryl group. Structures of such adducts were fixed under acidic conditions and then discussed by NMR spectroscopy as well as absorbance and fluorescence spectra. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：2919 / 2924

页数：6

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