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全碳 -13 糖的核磁共振:在一种新型天然糖 1,5 - 脱水果糖分析方法开发中的应用

NMR of all-carbon-13 sugars: an application in development of an analytical method for a novel natural sugar, 1,5-anhydrofructose.

作者信息

Kametani S, Mizuno H, Shiga Y, Akanuma H

机构信息

Department of Life Science, Graduate School of Arts and Sciences, The University of Tokyo, Komaba, Meguro-ku.

出版信息

J Biochem. 1996 Jan;119(1):180-5. doi: 10.1093/oxfordjournals.jbchem.a021206.

DOI:10.1093/oxfordjournals.jbchem.a021206
PMID:8907194
Abstract

Of the all-carbon-13 compounds, glucose is one of the most easily accessible, and therefore we applied 13C-NMR technique to the metabolic study of glucose-related compounds, 1,5-anhydro-D-glucitol and 1,5-anhydro-D-fructose (AF). Applying an INADEQUATE method to the substitutes of these novel sugars fully labeled with carbon-13, we could trace out the entire carbon skeleton with high sensitivity and confirm the chemical structures of these sugars. The method also provided a much easier way to optimize the enzymatic oxidation for AF preparation: we selectively and continuously monitored the quantities, as well as their structures in aqueous solution, of the substrate and products in a noninvasive manner. Similarly relying upon information from the 13C-NMR, we developed a valuable derivatization method of AF for its GC-MS application, which was so sensitive that we were able to demonstrate the natural occurrence of AF in rat liver.

摘要

在所有含碳-13的化合物中,葡萄糖是最容易获取的化合物之一,因此我们将碳-13核磁共振技术应用于与葡萄糖相关的化合物、1,5-脱水-D-葡萄糖醇和1,5-脱水-D-果糖(AF)的代谢研究。将异核单量子关联谱方法应用于这些完全用碳-13标记的新型糖类的替代物上,我们能够以高灵敏度追踪出整个碳骨架,并确认这些糖类的化学结构。该方法还提供了一种更简便的方式来优化用于制备AF的酶促氧化反应:我们以非侵入性方式选择性地、持续地监测水溶液中底物和产物的量及其结构。同样依靠来自碳-13核磁共振的信息,我们开发了一种用于AF气相色谱-质谱联用分析的有价值的衍生化方法,该方法灵敏度极高,以至于我们能够证明AF在大鼠肝脏中的天然存在。

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NMR of all-carbon-13 sugars: an application in development of an analytical method for a novel natural sugar, 1,5-anhydrofructose.全碳 -13 糖的核磁共振:在一种新型天然糖 1,5 - 脱水果糖分析方法开发中的应用
J Biochem. 1996 Jan;119(1):180-5. doi: 10.1093/oxfordjournals.jbchem.a021206.
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Effects of 1,5-anhydro-D-fructose on selected glucose-metabolizing enzymes.1,5-脱水-D-果糖对特定葡萄糖代谢酶的影响。
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Oxidation of 1,5-anhydro-D-glucitol to 1,5-anhydro-D-fructose catalyzed by an enzyme from bacterial membranes.细菌膜中的一种酶催化1,5-脱水-D-葡萄糖醇氧化为1,5-脱水-D-果糖。
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Dimeric dihydrodiol dehydrogenase is an efficient primate 1,5-anhydro-D-fructose reductase.二聚体二氢二醇脱氢酶是一种高效的灵长类 1,5-脱水-D-果糖还原酶。
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1,5-Anhydro-D-fructose; a versatile chiral building block: biochemistry and chemistry.
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Preparation and reactivity of a novel disaccharide, glucosyl 1,5-anhydro-D-fructose (1,5-anhydro-3-O-alpha-glucopyranosyl-D-fructose).一种新型二糖——葡萄糖基1,5-脱水-D-果糖(1,5-脱水-3-O-α-D-吡喃葡萄糖基-D-果糖)的制备及反应活性
Carbohydr Res. 2003 Oct 10;338(21):2221-5. doi: 10.1016/s0008-6215(03)00341-0.
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1,5-anhydro-D-fructose and its derivatives: biosynthesis, preparation and potential medical applications.1,5-脱水-D-果糖及其衍生物:生物合成、制备和潜在的医学应用。
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Catabolism of 1,5-anhydro-D-fructose in Sinorhizobium morelense S-30.7.5: discovery, characterization, and overexpression of a new 1,5-anhydro-D-fructose reductase and its application in sugar analysis and rare sugar synthesis.苜蓿中华根瘤菌S-30.7.5中1,5-脱水-D-果糖的分解代谢:一种新型1,5-脱水-D-果糖还原酶的发现、表征、过表达及其在糖分析和稀有糖合成中的应用
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Hepatic production of 1,5-anhydrofructose and 1,5-anhydroglucitol in rat by the third glycogenolytic pathway.大鼠肝脏通过第三条糖原分解途径生成1,5-脱水果糖和1,5-脱水葡萄糖醇。
Eur J Biochem. 1996 Dec 15;242(3):832-8. doi: 10.1111/j.1432-1033.1996.0832r.x.

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Hypothesis: A Novel Neuroprotective Role for Glucose-6-phosphatase (G6PC3) in Brain-To Maintain Energy-Dependent Functions Including Cognitive Processes.假说:葡萄糖-6-磷酸酶(G6PC3)在大脑中具有新的神经保护作用——维持依赖能量的功能,包括认知过程。
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