¹³C₆-glucose | 40010-57-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ¹³C₆-glucose
• 英文别名: Dextrose-13C6；(2S,3R,4S,5S,6R)-6-(hydroxy(113C)methyl)(2,3,4,5,6-13C5)oxane-2,3,4,5-tetrol
• CAS: 40010-57-9
• 化学式: C₆H₁₂O₆
• 分子量: 186.092
• InChiKey: WQZGKKKJIJFFOK-YPYOLYKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  110
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ¹³C₆-glucose 以87%的产率得到1,2:5,6-di-O-isopropylidene-α-D-(U-¹³C)glucofuranose
  参考文献：
  名称：

  Stable isotope-labeled amino acid, method of integrating the same into target protein, method of NMR structural analysis of protein

  摘要：

  公开号：

  EP1457482B1
• 作为产物：
  描述：

  α,α-trehalose-(13)C12 在 硫酸 、 水 作用下， 反应 6.0h， 生成 β-D-glucose 、 ¹³C₆-glucose
  参考文献：
  名称：

  Biosynthesis of glucose-d-13C6 from Hansenula polymorpha and methanol-13C

  摘要：

  本文介绍了一种简单有效的方法，即利用富含 99% 甲醇-13C 的养甲酵母 Hansenula polymorpha 通过发酵合成葡萄糖-d-13C6。利用甲醇-13C 作为唯一的碳源，H. polymorpha 可以在不利的生长条件下积累大量的 α,α-三卤糖-13C12；然后三卤糖可被水解，得到 13C 丰度为 98.5% 的葡萄糖-d-13C6。Copyright © 2011 John Wiley & Sons, Ltd. All Rights Reserved.

  DOI：

  10.1002/jlcr.1935

文献信息

• Biosynthesis of riboflavin
  作者：Paul J. Keller、Quang Le Van、Adelbert Bacher、Heinz G. Floss

  DOI：10.1016/s0040-4020(01)88657-9

  日期：1983.1

  Several recently developed NMR techniques were used to analyze samples of biosynthetically labeled riboflavin tetraacetate. The xylene ring of riboflavin consists of two biogenetically identical halves arising from dismutation of a lumazine precursor. The origin of the four carbons which eventually form this xylene ring eas investigated. Carbon-13 labeled precursors were fed to growing cultures of

  几种最近开发的NMR技术用于分析生物合成标记的核黄素四乙酸盐的样品。核黄素的二甲苯环由两个生物上完全相同的半部分组成，这两个半部分是通过先天鲁嗪的歧化而形成的。研究了最终形成该二甲苯环的四个碳的起源。碳13标记的前体被喂入棉铃兰生长的培养物中，分离出产生的核黄素并进行乙酰化。由于存在许多13 C- 13，衍生自[U- 13 C 6 ]葡萄糖的核黄素四乙酸盐样品具有复杂的13 C- NMR光谱。C联轴器和重叠的多重峰。类似于质子实验所进行的13 C-单核-J光谱简化了该材料的光谱分析。可以看到各个13 C多重峰，将数据投影到13 C化学位移轴上会产生13 C NMR光谱，该光谱同时被13 C和1 H宽带解耦（正常的1 H宽带解耦为整个使用）。甲13 C-同核-2D-化学位移相关性光谱用来确定在核糖醇基侧链偶联伴侣。但是，2D-INADEQUATE更适合于确定整个光谱的碳-碳连通性。这三种技术的结合允许进行明确的13
• Chemical synthesis of allyl-[13C6]-glucuronate
  作者：Bachir Latli、Matt Hrapchak、Ravikumar Seetharama、Dhileepkumar Krishnamurthy、Chris H. Senanayake

  DOI：10.1002/jlcr.1875

  日期：2011.5.30

  The synthesis of allyl-[13C6]-glucuronate from α-D-[13C6]-glucose in five steps is described. Selective protection of the primary alcohol in the glucose with the bulky trityl group followed by acetylation in the same pot gave the fully protected sugar. Removal of the trityl group followed by oxidation of the primary alcohol to the acid and removal of the acetate groups using catalytic amounts of sodium methoxide gave the glucuronic acid. Reaction with allyl bromide using resin-bound fluoride gave the title compound. Copyright © 2011 John Wiley & Sons, Ltd.

  本文介绍了通过五个步骤从 α-D-[13C6]- 葡萄糖合成烯丙基-[13C6]-葡萄糖醛酸酯的过程。先用笨重的三苄基对葡萄糖中的伯醇进行选择性保护，然后在同一锅中进行乙酰化，得到完全保护的糖。去除三苯甲基，然后将伯醇氧化成酸，再用甲醇钠催化去除乙酸基团，就得到了葡萄糖醛酸。使用树脂结合的氟化物与烯丙基溴反应，可得到标题化合物。Copyright © 2011 John Wiley & Sons, Ltd. All Rights Reserved.
• C3 Epimerization of Glucose, via Regioselective Oxidation and Reduction
  作者：Varsha R. Jumde、Niek N. H. M. Eisink、Martin D. Witte、Adriaan J. Minnaard

  DOI：10.1021/acs.joc.6b02074

  日期：2016.11.18

  Palladium-catalyzed oxidation can single out the secondary hydroxyl group at C3 in glucose, circumventing the more readily accessible hydroxyl at C6 and the more reactive anomeric hydroxyl. Oxidation followed by reduction results in either allose or allitol, each a rare sugar that is important in biotechnology. Also, N-acetylglucosamine is selectively oxidized at C3. These results demonstrate that

  钯催化的氧化可以选出葡萄糖中C3处的仲羟基，从而避开了C6处更容易接近的羟基和反应性更高的异头羟基。氧化然后还原导致异位糖或异丁醇，每一种都是在生物技术中很重要的稀有糖。同样，N-乙酰氨基葡糖在C3处被选择性地氧化。这些结果表明，葡萄糖和N-乙酰氨基葡糖是最容易获得的手性结构单元，在均相催化中可以是通用底物。
• Chemoenzymatic synthesis of GM3, Lewis x and sialyl Lewis x oligosaccharides in 13C-enriched form
  作者：Mark A. Probert、Mark.J. Milton、Richard Harris、Sergio Schenkman、Jonathan M. Brown、Steven W. Homans、Robert A. Field

  DOI：10.1016/s0040-4039(97)01304-x

  日期：1997.8

  In connection with studies on the solution and protein-bound conformation of oligosaccharides, we had reason to consider the application of C-13-enriched sugars. Herein we describe the synthesis of ganglioside GM(3) trisaccharide (1), Lewis x trisaccharide (2) and the sialyl Lewis x tetrasaccharide (3) from [U-C-13]-D-Glc, [U-C-13]-L-Gal and [U-C-13]-pyruvate. (C) 1997 Elsevier Science Ltd.
• Rapid Preparation of Isotopolog Libraries by in Vivo Transformation of ¹³C-Glucose. Studies on 6,7-Dimethyl-8-ribityllumazine, a Biosynthetic Precursor of Vitamin B₂
  作者：Boris Illarionov、Markus Fischer、Chan Yong Lee、Adelbert Bacher、Wolfgang Eisenreich

  DOI：10.1021/jo0493222

  日期：2004.8.1

  An Escherichia coli strain engineered for expression of the ribABGH genes of Bacillus subtilis was shown to produce 100 mg of the riboflavin precursor 6,7-dimethyl-8-ribityllumazine per liter of minimal medium. Growth of the recombinant strain in medium supplemented with [U-C-13(6)]glucose and/or (NH4Cl)-N-15 as single sources of carbon and/or nitrogen afforded 6,7-dimethyl-8-ribityllumazine universally labeled with C-13 and/or N-15. The yield of [U-C-13(13)]-6,7-dimethyl-8-ribityllumazine based on [U-C-13(6)]glucose was 25 mg/g. Fermentation with [1-C-13(1)]-, [2-C-13,]-, or [3-C-13(1)]glucose afforded mixtures of 6,7-dimethyl-8-ribityllumazine isotopologs, predominantly with C-13 enrichment of single carbon atoms. The isotope-labeled samples enabled a comprehensive NMR analysis of 6,7-dimethyl-8-ribityllumazine. Isotopolog libraries of a wide variety of microbial metabolites can be produced by the same experimental approach.