D-葡萄糖-4-13C | 84270-10-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: D-葡萄糖-4-13C
• 英文名称: D-4-(13)C-glucose
• 英文别名: [4-13C1]glucose；[4-13C]-glucose；D-[4-13C]Glucose；(3R,4S,5S,6R)-6-(hydroxymethyl)(513C)oxane-2,3,4,5-tetrol
• CAS: 84270-10-0
• 化学式: C₆H₁₂O₆
• 分子量: 181.147
• InChiKey: WQZGKKKJIJFFOK-CDAWROFUSA-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

制备方法与用途

葡萄糖-13C-1（即D-葡萄糖-13C-1）是一种带有13C标记的D-葡萄糖。葡萄糖作为单糖，是生物学中重要的碳水化合物。D-葡萄糖不仅是一种甜味剂和代谢的关键成分，还与细胞代谢状态以及生物和非生物应激反应密切相关，是关键信号分子之一[1]。

反应信息

• 作为反应物：
  描述：

  尿苷-5'-三磷酸 、 D-葡萄糖-4-13C 在 hexokinase (EC 2.7.1.1) 、 phosphoglucomutase (EC 5.4.2.2) 、 uridine-5'-diphosphoglucose pyrophosphorylase (EC 2.7.7.9) 作用下， 以 水 为溶剂， 生成 uridine diphospho-[4-13C]-glucose
  参考文献：
  名称：

  High yielding one-pot enzyme-catalyzed synthesis of UDP-glucose in gram scales

  摘要：

  Uridine diphosphoglucose is an important cofactor of glucosylating enzymes. A simple and high yielding one-pot enzymatic synthesis of UDPG on a gram scale from glucose via hexokinase, phosphoglucomutase and UDPG pyrophosphorylase (UGPase) is described. Repetitive addition of substrate was used to avoid inhibition of UGPase. The approach allows recovery of active enzymes and their re-use. The synthesis of UDP-[4-C-13]-glucose on a 0.5 g scale resulted in a final yield of 70% and a purity of > 95% after chromatographic purification. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00122-7

文献信息

• Gas-Phase Intercluster Thiyl-Radical Induced C–H Bond Homolysis Selectively Forms Sugar C2-Radical Cations of Methyl D-Glucopyranoside: Isotopic Labeling Studies and Cleavage Reactions
  作者：Sandra Osburn、Gaetano Speciale、Spencer J. Williams、Richard A. J. O’Hair

  DOI：10.1007/s13361-017-1667-2

  日期：2017.7.1

  exchangeable OH and NH protons with deuterons reveals that the sugar radical cation is formed in a process involving abstraction of a hydrogen atom from a C-H bond of the sugar coupled with proton transfer to the sugar, to form [M - H• + D+]. Investigation of this process using individual C-D labeled sugars reveals that the main site of H/D abstraction is the C2 position, since only the C2-deuterium

  一组甲基D-吡喃葡萄糖苷的同位素异构体与多级质谱实验结合使用，以确定通过最近开发的“生物启发”方法形成的糖自由基阳离子的自由基位点和裂解反应。在CID（MS2）的第一阶段，糖和S-亚硝基半胱胺[H3NCH2CH2SNO + M] +之间的质子化非共价复合物的碰撞诱导解离（CID）通过键均解释放硫代自由基，得到非共价自由基阳离子，[H3NCH2CH2S•+ M] +。该自由基阳离子复合物的CID（MS3）导致非共价复合物解离，生成糖自由基阳离子。用氘核取代所有可交换的OH和NH质子表明，糖自由基阳离子是在一个过程中形成的，该过程涉及从糖的CH键中夺取氢原子，然后将质子转移到糖中，从而形成[M-H•+ D +]。使用单个CD标记的糖对此过程进行的研究表明，H / D提取的主要位点是C2位置，因为只有C2氘标记的糖会产生占主导地位的[M-D•+ H +]产物离子。通过另一阶段的CID（MS4）研究了二糖糖基阳离子[M-H•+
• Mechanism of Brønsted Acid-Catalyzed Glucose Dehydration
  作者：Liu Yang、George Tsilomelekis、Stavros Caratzoulas、Dionisios G. Vlachos

  DOI：10.1002/cssc.201403264

  日期：2015.4.24

  the rate‐limiting step is the first dehydration of protonated glucose and that the majority of glucose is consumed through the HMF intermediate. We introduce a combination of 1) automatic mechanism generation with isotopic tracing experiments and 2) elementary reaction flux analysis of important paths with NMR spectroscopy and kinetic experiments to assess mechanisms. We find that the excess formic acid

  我们介绍了第一个基于DFT的微动力学模型，用于布朗斯台德酸催化的葡萄糖向葡萄糖转化为5-羟甲基糠醛（HMF），乙酰丙酸（LA）和甲酸（FA）的转化，并主要在低转化率下进行动力学和同位素示踪NMR光谱分析。我们揭示葡萄糖通过循环路径脱水。我们的建模结果与动力学数据非常吻合，表明限速步骤是质子化葡萄糖的首次脱水，并且大部分葡萄糖是通过HMF中间体消耗的。我们介绍了1）结合同位素示踪实验自动生成机理，以及2）利用NMR光谱学和动力学实验对重要路径进行基本反应通量分析以评估机理的方法。我们发现过量的甲酸，
• Rapid One-Pot Synthesis of Riboflavin Isotopomers
  作者：Werner Römisch、Wolfgang Eisenreich、Gerald Richter、Adelbert Bacher

  DOI：10.1021/jo026105x

  日期：2002.12.1

  Flavocoenzymes labeled with stable isotopes are important reagents for the study of flavoproteins using isotope-sensitive methods such as NMR, ENDOR, infrared, and Raman spectroscopy. We describe highly versatile one-pot methods for the preparation of riboflavin isotopomers labeled with C-13 in every desired position of the xylene moiety. The starting materials are commercially available C-13-labeled glucose samples, which are converted into riboflavin using enzymes of the oxidative pentose phosphate pathway in combination with recombinant enzymes of the riboflavin biosynthetic pathway. The overall reaction comprises six enzyme-catalyzed reaction steps for the synthesis of the vitamin and two auxiliary enzymes for in situ recycling of cofactors. The overall yields of riboflavin based on isotope-labeled glucose are 35-50%.
• High yielding one-pot enzyme-catalyzed synthesis of UDP-glucose in gram scales
  作者：Xueyan Ma、Joachim Stöckigt

  DOI：10.1016/s0008-6215(01)00122-7

  日期：2001.7

  Uridine diphosphoglucose is an important cofactor of glucosylating enzymes. A simple and high yielding one-pot enzymatic synthesis of UDPG on a gram scale from glucose via hexokinase, phosphoglucomutase and UDPG pyrophosphorylase (UGPase) is described. Repetitive addition of substrate was used to avoid inhibition of UGPase. The approach allows recovery of active enzymes and their re-use. The synthesis of UDP-[4-C-13]-glucose on a 0.5 g scale resulted in a final yield of 70% and a purity of > 95% after chromatographic purification. (C) 2001 Elsevier Science Ltd. All rights reserved.