Improved Synthesis of Firefly D-Luciferyl-D-adenylate : A Key Intermediate of Firefly Bioluminescence(Organic Chemistry)
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概要
- 論文の詳細を見る
The title compound was obtained by McElroy et al. as a crude product without definite characterization due to its instability and the lack of a suitable analytical method other than bioluminescence. In this research, reliable methods for analyzing and isolating the unstable luciferyladenylates were established by means of HPLC. Firefly L-luciferin was condensed with adenylic acid, the chiral center of L-luciferin being epimerized whe adenylated. After evaporating the solvent, the residue was washed with EtOAc and CH_2Cl_2, and extracted with 6M urea. The extract was chromatographed on a reversed-phase C_<18>-HPLC column. The D-luciferyl-D-adenylate contained less than 8% luciferin and its diastereomeric purity was more than 98%. The luciferyladenylates are extremely unstable; they are hydrolyzed to luciferin and adenylic acid, and epimerized quite easily in neutral to basic buffers. L-Luciferyl-D-adenylate emits light with firefly luciferase of about 1/3 the light yield compared to that of the D,D-isomer, possibly because of partial epimerization of the L,D-isomer to the D,D-isomer during the reaction.
- 社団法人日本農芸化学会の論文
- 1988-11-23
著者
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Imai Kunio
Laboratory Of Bioorganic Chemistry Graduate School Of Bioresources Mie University
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Imai Kunio
Laboratory Of Organic Chemistry Faculty Of Agriculture Nagoya University:(present Office)laboratory
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Goto T
Department Of Agricultural Chemistry Faculty Of Agriculture Nagoya University
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Goto Toshio
Laboratory Of Organic Chemistry Faculty Of Agriculture Nagoya University
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