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

スポンサーリンク

概要

• 論文の詳細を見る

• 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

関連論文

• Cytotoxicity of Extracts from Alternaria alternata against Cultured Tobacco BY-2 Cells
• Distinctive Effects of Menadione on the In Vivo Catalase Activity and the Adaptation to Hydrogen Peroxide Stress in Yeast Cells
• Intracellular Fate of 2-NBDG, a Fluorescent Probe for Glucose Uptake Activity, in Escherichia coli Cells
• RFLP Analysis of the Internal Transcribed Spacer Regions of Sporothrix schenckii
• A Japanese Case of Tinea Corporis Caused by Arthroderma benhamiae
• Cell-lytic Activity of Tobacco BY-2 Induced by a Fungal Elicitor from Alternaria alternata Attributed to the Expression of a Class I β-1, 3-Glucanase Gene
• Isolation of a Novel Isozyme of Tobacco BY-2 Chitinase Induced by a Fungal Elicitor
• PJ-731 Genetic Disruption of All Nitric Oxide Synthase Isoforms Causes Accelerated Renal Lesion Formation in Mice in Vivo(PJ123,Kidney/Renal Circulation/CKD 6 (H),Poster Session (Japanese),The 73rd Annual Scientific Meeting of The Japanese Circulation Soc
• Delection of Antifungal Activity in Belamcanda chinensis by a Single-cell Bioassay Method and Isolation of Its Active Compound, Tectorigenin
• Upstream-directed Growth of Filamentous Fungi in a Flowing Medium
• タバコ培養細胞細胞間膜への定量的傷害印加のための微小電極システムの応用
• Real Time α Value Measurement with Feynman-α Method Utilizing Time Series Data Acquisition on Low Enriched Uranium System
• Modifications Associated with Use of the Benzyloxymethyl Group on Histidine
• Simultaneous Imaging of Multiple Fluorescent Probes in Bio-Cells
• Vitamin B12 Promotes Cx40 and HCN4 Gene Expression at an Early Stage of Cardiomyocyte Differentiation
• Kinetic Basis for the Donor Nucleotide-Sugar Specificity of β1,4-N-Acetylglucosaminyltransferase III^1
• ＜Poster＞Synthesis of 2-NBDLG, the antipode of fluorescent D-glucose tracer 2-NBDG
• ＜Symposium I＞A new imaging method of glucose transport in live cells
• Sensitive Detection of Antifungal Activity of Volatile Components Emitted from Plant Leaf Samples by Single Hypha Assay Method
• Evaluation of Antifungal Activity of an Antifungal Drug by In Vitro Simulation of In Vivo Pharmacokinetics of the Drug against Fungal Hyphal Growth
• Rapid and Sensitive Screening of Antifungal Activity in Medicinal Plants by a Single-cell Biosensing System
• Cloning, Expression, and Transglycosylation Reaction of Paenibacillus sp. Strain W-61 Xylanase 1
• 電気的シグナルによるイネ単一細胞内へのCa〔2+〕流入の制御
• Automatic Mapping of Viable Microbial Cells Distributed in the Surface Layer of Cotton Fabrics
• Viable Cell Detection by the Combined Use of Fluorescent Glucose and Fluorescent Glycine(Food & Nutrition Sience)
• タバコ培養細胞における膜電位制御と膜インピーダンスの同時計測
• Functional Analysis of a Rice Putative Voltage-Dependent Ca^ Channel, OsTPC1, Expressed in Yeast Cells Lacking its Homologous Gene CCH1
• Vapor-Phase Ethylation of Biphenyl over MTW Zeolites
• Evidence for the plasma membrane localization of a putative voltage-dependent Ca2+ channel, OsTPC1, in rice
• Single-Cell Imaging of the Ca^2+ Influx into Bovine Endothelial Cells Occurring in Response to an Alternating Electric
• Comprehensive Analysis of Glucan Elicitor-Regulated Gene Expression in Tobacco BY-2 Cells Reveals a Novel MYB Transcription Factor Involved in the Regulation of Phenylpropanoid Metabolism
• CBF Change Evoked by Somatosensory Activation Measured by Laser-Doppler Flowmetry: Independent Evaluation of RBC Velocity and RBC Concentration
• The Internalization and Metabolism of 3-Deoxyglucosone in Human Umbilical Vein Endothelial Cells
• Synthesis of HS-toxin A Aglycone
• Evaluation of a New Most-Probable-Number (MPN) Dilution Plate Method for the Enumeration of Escherichia coli in Water Samples
• Complete Disruption of All Nitric Oxide Synthase Genes Causes Markedly Accelerated Renal Lesion Formation Following Unilateral Ureteral Obstruction in Mice In Vivo
• Syntheses of Stem Peptides of Bacterial Cell Walls with Proinflammatory Activity
• Influence of antifungal pre-treatment in preparing test mycelium on MIC values of several antifungal agents against Aspergillus niger
• Production of a Cloned Mouse by Nuclear Transfer from a Fetal Fibroblast Cell of a Mouse Closed Colony Strain
• Isolation and Properties of an Extracellular β-Glucosidase from a Filamentous Fungus, Cladosporium resinae, Isolated from Kerosene
• Synthesis of Marinostatin, an Ester-Linked Protein Protease Inhibitor from the Marine Bacterium Pseudoalteromonas sagamiensis
• Suppression of Side Reactions during Final Deprotection Employing a Strong Acid
• Theoretical Verification of the Trapped Neutron Catalyzed Model of Deuteron Fusion in Pd/D and Ti/D Systems
• Cloning, Expression, and Transglycosylation Reaction of Paenibacillus sp. Strain W-61 Xylanase 1
• Development of a Density Slicer for the Simple Collection of Respective Density Layers after Stepwise Density Gradient Centrifugation
• Separation of Viable Histamine-Producing Bacteria from Yellowtail Meat Components by Density Gradient Centrifugation
• Adaptation of Aspergillus niger to Multiple Agents Whose Action Mechanisms are Different
• Intraoperative hemodynamic management for minimally invasive direct coronary bypass: two case reports
• MECHANISM OF INHIBITION OF CASPASE-3 ACTIVITY IN STARFISH UNFERTILIZED EGGS(Developmental Biology,Abstracts of papers presented at the 76^ Annual Meeting of the Zoological Society of Japan)
• CASPASE-3 INHIBITOR IN STARFISH IMMATURE OOCYTES(Developmental Biology,Abstracts of papers presented at the 74^ Annual Meeting of the Zoological Society of Japan)
• QUANTIFICATION OFIN VIVO CASPASE-3 ACTIVITY IN AN APOPTOTIC STARFISH EGG USING MEMBRANE-IMPERMEANT SUBSTRATE(Developmental Biology)(Proceeding of the Seventy-Third Annual Meeting of the Zoological Society of Japan)
• Synthesis of O-Linked β-N-Acetylglucosamine-Containing Peptides by the Boc Strategy Employing the HF Procedure for Final Deprotection
• SOLID PHASE SYNTHESIS OF THE ANTIBACTERIAL GLYCOPEPTIDE, FORMAECIN USING BOC-STRATEGY
• PC77 TOTAL SYNTHESIS OF SPIDER TOXIN, NSTX-3 AND ITS STRUCTURE-ACTIVITY RELATIONSHIP
• The Crystal Structure of the Collagen Model Peptide containing 4(S)-hydroxyproline-proline-glycine Repeats
• Synthesis of a lysyl tyrosylquinone fragment of crosslinked cofactor in lysyl oxidase
• Evidence for the plasma membrane localization of a putative voltage-dependent Ca^ channel, OsTPC1, in rice
• Gradient of bronchial end-tidal CO_2 during two-lung ventilation in lateral decubitus position is predictive of oxygenation disorder during subsequent one-lung ventilation
• Cuff occlusion on the left upper arm increases flow of the left internal mammary artery and bypass flow to the left anterior descending artery
• Chromosome Abnormality in Human Gametes by Exposure to Mutagens (特別企画 〔日本環境変異原学会〕第24回大会ミニシンポジウム) -- (ヒト集団の環境影響モニタリング)
• Chemical Synthesis of the SUMOylated GARP Domain for Functional Analysis of PHR1 Protein Involved in Phosphate Starvation Regulation in Vascular Plants
• Structure-Activity Relationship of Marinostatin, an Ester-Linked Serine Protease Inhibitor
• Hedyotide B1 : Intein-Mediated Synthesis of Thioester Presursor and Optimization of Cyclization and Oxidative Folding of a Novel Cyclotide
• 単一細胞実験法のためのマイクロバイオエレクトロニクス
• Solid Phase Synthesis of Glycopeptide Using Boc-Strategy
• Improved Synthetic Method of Nephritogenic Glycopeptide, Nephritogenoside
• Propofol Protects against Anandamide-Induced Injury in Human Umbilical Vein Endothelial Cells
• Lanthanoid Exchanged Mordenites as Catalysts for the Isopropylation of Biphenyl
• Carpal spasm observed during and after sevoflurane anesthesia
• The effect of propofol infusion on minimum alveolar concentration of sevoflurane for smooth tracheal intubation
• Increased incidence of spontaneous malformations in pups and increased litter size from pinealectomized dams
• "Small bound isomorphisms on the domain of a closed^(*)-derivation in C(K)
• Complete Disruption of All Nitric Oxide Synthase Genes Causes Markedly Accelerated Renal Lesion Formation Following Unilateral Ureteral Obstruction in Mice In Vivo
• Synthesis of α-Aminophosphonic Octapeptide, Phe-Gly-Ser-Leu-Ala^p-Phl-Leu-Pro, an Analog with Partial Sequence of arb B-2 Gene Product
• Does the Location of the Motor Point Identified with Electrical Stimulation Correspond to that Identified with the Gross Anatomical Method?
• 単一細胞バイオエレクトロケミストリーを目指す高効率マイクロインジェクション技術
• Chromosome analysis of human spermatozoa with morphologically abnormal heads by injection into mouse oocytes
• Effects of Systemic Deep Hypothermia and Subarachnoid Block on the Longitudinally Conducting Evoked Spinal Cord Potentials in Man
• A Physico-Chemical Approach toward the Oligomerization Mechanism of Adiponectin with Its Collagen Like Domain Peptide
• Application of N^π-4-Methoxybenzyloxymethylhistidine to Fmoc Peptide Synthesis
• ES細胞分化のFACS解析における蛍光グルコース2-NBDGの代謝活性指標としての利用
• Effect of Higher-Harmonic Flux in Exponential Experiment for Subcriticality Measurement
• Analysis of Odor Compounds in Feces of Mice that Were Exposed to Various Stresses during Breeding
• Development of a Protocol for Selection of GenesFit for the In Vivo Knockdown Method and its Application to Insulin Receptor Substrate Genesin Mice
• Potential Use of Lactobacillus Cell Density in Feces as a Non-invasive Bio-indicator for Evaluating Environmental Stress During Mouse Breeding
• Chemical studies on tuberactinomycin. XI. Semisyntheses of tuberactinomycin analogs with various amino acids in branched part.
• The structure of galantinamic acid, a new amino acid in a peptide antibiotic galantin I.
• Chemical studies on tuberactinomycin. XIV. Novel synthesis of DL-capreomycidine.
• Structural and stereochemical study of galantinic acid, a new amino acid from peptide antibiotic galantin I.
• Chemical Studies on Tuberactinomycin. VII. Synthesis of γ-Hydroxy-β-lysine
• Automatic Stop of a Microinjector Distinctively in the Cytosol or the Vacuole of Plant Single-cells
• Synthesis of Acyl Derivatives of β-Lysine for Peptide Synthesis
• Synthesis of L-epicapreomycidine.
• Chemical studies on tuberactinomycin. XVII. Synthesis of threo-.GAMMA.-hydroxy-L-.BETA.-lysine, constituent amino acid of tuberactinomycin A and N.
• Electric Gene Expression in Single-cells of Rice Protoplast via Ca2+ Entering the Cell
• Development of Efficient Synthetic Protocol for Fmoc Amino Acid-Incorporated N-Sulfanylethyl-Aniline Linker as Peptide Thioester Precursor
• Application of 4-Methoxybenzyloxymethylcysteine in Fmoc Solid Phase Peptide Synthesis
• A Fluorescent Assay Method for GDP-L-Fuc:N-Acetyl-.BETA.- D-Glucosaminide .ALPHA.1-6Fucosyltransferase Activity, Involving High Performance Liquid Chromatography.
• Development of a Protocol for Selection of Genes Fit for the In Vivo Knockdown Method and its Application to Insulin Receptor Substrate Genes in Mice
• Analysis of Odor Compounds in Feces of Mice that Were Exposed to Various Stresses during Breeding

もっと見る 閉じる

スポンサーリンク