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

概要

D-Glucose is one of the most important energy sources for the survival of various organisms, from E. colito 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 invarious research fi elds. For the last ten years, however, researchers have awaited an optical control substance forevaluating the extent of non-specifi c adsorption of 2-NBDG upon plasma membrane and/or the rate of unhealthy2-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 commerciallyavailable. Although a few papers on the synthesis of L-glucosamine have been reported, a new synthetic method ofL-glucosamine should be absolutely required in practical view of optical purity and preparative scale. We convertedcommercially available L-mannose into desired L-glucosamine by 10 steps in 14% of overall yield. The 1H-NMRdata 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 ofD-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 confocalmicroscopy, should provide valuable information on dynamism of glucose transport.

著者

MATSUOKA HIDEAKI Department of Biotechnology, Faculty of Technology, Tokyo University of Agriculture and Technology
WATANABE Seiji Department of Dermatology, Kanazawa Medical University
Matsuoka Hideaki Department Of Biotechnology And Life Science Faculty Of Technology Tokyo University Of Agriculture A
Yamamoto Toshihiro Saito Res. Center Peptide Institute Inc. Ibaraki Osaka
Suga Sechiko Center Res. & Edu. Lifelong Learning Hirosaki Univ.
Yamada Katsuya Dept. Physiol. Hirosaki Univ. Grad. Sch. Med.
Yamada Katsuya Department Of Physiology School Of Medicine Akita University
Nishiuchi Yuji Saito Res. Center Peptide Institute Inc. Ibaraki Osaka
TESHIMA Tadashi Peptide Institute, Protein Research Foundation
Teshima Tadashi Saito Research Center, Peptide Institute, Inc., Ibaraki
Teshima T Saito Res. Center Peptide Institute Inc. Ibaraki Osaka
Watanabe Seiji Department Of Anatomical Science Hirosaki Univ. Grad. Sch. Med.
Teshima Tadashi Saito Research Center Peptide Institute Inc.
Teshima Tadashi Department Of Chemistry Faculty Of Science Osaka University
Teshima Tadashi Peptide Institute Protein Research Foundation
Watanabe Seiji Department Of Agricultural Chemistry Faculty Of Agriculture Tohoku University:(present Address) Show
Teshima Tadashi SAITO Res. Center, Peptide Institute, Inc., Ibaraki,Osaka

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