＜Poster＞Synthesis of 2-NBDLG, the antipode of fluorescent D-glucose tracer 2-NBDG

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  • Synthesis of 2 NBDLG the antipode of fluorescent D glucose tracer 2 NBDG

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D-Glucose is one of the most important energy sources for the survival of various organisms, from E. coli to mammals. For live-cell monitoring of glucose uptake at the single-cell level, a fl uorescent D-glucose derivative 2-[N-（7-nitrobenz-2-oxa-1,3-diazol-4- yl）amino]-2-deoxy-D-glucose [2-NBDG], which we developed, has been widely used in various research fi elds. For the last ten years, however, researchers have awaited an optical control substance for evaluating the extent of non-specifi c adsorption of 2-NBDG upon plasma membrane and/or the rate of unhealthy 2-NBDG uptake through partially（ or transiently） damaged membrane. 　Here we introduce a fluorescent L-glucose derivative, 2-[N（- 7-Nitrobenz-2-oxa- 1,3-diazol-4-yl）amino]- 2-deoxy-Lglucose [2-NBDLG]. L-Glucosamine is a key intermediate toward the synthesis of 2-NBDLG, but not commercially available. Although a few papers on the synthesis of L-glucosamine have been reported, a new synthetic method of L-glucosamine should be absolutely required in practical view of optical purity and preparative scale. We converted commercially available L-mannose into desired L-glucosamine by 10 steps in 14% of overall yield. The 1H-NMR data of synthetic L-glucosamine were completely identical with those of commercially available D-glucosamine. On the other hand, optical purity of L-glucosamine was confi rmed by comparison of specifi c rotation with that of D-glucosamine. L-Glucosamine thus obtained was coupled with NBD-halide to give 2-NBDLG. Use of transporterrecognizable （D-isomer） and unrecognizable （L-isomer） fluorescent analogues combined with real-time confocal microscopy, should provide valuable information on dynamism of glucose transport.

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  • 弘前医学

    弘前医学 61 (Supplement), S187-S191, 2010-07-08

    弘前大学大学院医学研究科・弘前医学会

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