[C,1-2H]-D-ribofuranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [C,1-2H]-D-ribofuranose
• 英文别名: [1'-²H]ribose；d-Ribose-1-d；(3R,4R,5R)-2-deuteriooxane-2,3,4,5-tetrol
• 化学式: C₅H₁₀O₅
• 分子量: 151.123
• InChiKey: SRBFZHDQGSBBOR-ROIYBNBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  90.2
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [C,1-2H]-D-ribofuranose 在 硫酸 作用下， 以 甲醇 为溶剂， 生成 [1-2H]-D-ribose
  参考文献：
  名称：

  Biosynthesis of the thiamin pyrimidine: the reconstitution of a remarkable rearrangement reaction

  摘要：

  5-氨基咪唑核苷酸（AIR）转化为4-氨基-2-甲基-5-羟甲基嘧啶（HMP）的反应是细菌硫胺素生物合成途径中的一个迷人反应，可能是初级代谢中最复杂的未解决重排反应。我们已经成功地在无细胞系统中重构了这个反应。E. coli 的 thiC 基因产物以及一个额外的未鉴定的 E. coli 蛋白质是反应所必需的。此外，SAM 和烟酰胺辅因子也是完全活性所需的。我们描述了标记研究，以确定嘧啶中大多数原子的来源。基于这些研究，提出了一种 HMP 形成的新机制。

  DOI：

  10.1039/b405429f
• 作为产物：
  描述：

  2,3-O-异亚丙基-D-核糖酸 gamma-内酯 在 硼氘化钠 、 Amberlite IR 120 (H⁺) 作用下， 以 四氢呋喃 、 重水 、 乙腈 为溶剂， 反应 19.0h， 生成 [1-2H]-D-ribose 、 [C,1-2H]-D-ribofuranose
  参考文献：
  名称：

  D-XYLOSE (D-GLUCOSE) ISOMERASE (EC 5.3.1.5): OBSERVATIONS AND COMMENTS CONCERNING STRUCTURAL REQUIREMENTS OF SUBSTRATES AS WELL AS MECHANISTIC FEATURES

  摘要：

  In the course of investigations into the applicability of xylose isomerase as a reagent for carbohydrate synthesis, some questions raised in context with structural requirements for productive substrates as well as mechanistic considerations have been addressed. Amongst the interesting findings obtained so far is the observation that the enzyme requires two vicinal hydroxyl groups, either at positions C-3 and C-4 or at C-4 and C-5, for productive binding/catalysis. Furthermore, two apparently different reaction pathways occur in parallel when certain aldopentoses as well as selected aldohexoses are offered as substrates, this explaining the recently observed formation of epimeric aldoses together with the expected ketoses observed upon extended reaction times.

  DOI：

  10.1081/car-100104860

文献信息

• <scp>D</scp>-XYLOSE (<scp>D</scp>-GLUCOSE) ISOMERASE (EC 5.3.1.5): OBSERVATIONS AND COMMENTS CONCERNING STRUCTURAL REQUIREMENTS OF SUBSTRATES AS WELL AS MECHANISTIC FEATURES
  作者：Herwig Häusler、Hansjörg Weber、Arnold E. Stütz*

  DOI：10.1081/car-100104860

  日期：2001.4.30

  In the course of investigations into the applicability of xylose isomerase as a reagent for carbohydrate synthesis, some questions raised in context with structural requirements for productive substrates as well as mechanistic considerations have been addressed. Amongst the interesting findings obtained so far is the observation that the enzyme requires two vicinal hydroxyl groups, either at positions C-3 and C-4 or at C-4 and C-5, for productive binding/catalysis. Furthermore, two apparently different reaction pathways occur in parallel when certain aldopentoses as well as selected aldohexoses are offered as substrates, this explaining the recently observed formation of epimeric aldoses together with the expected ketoses observed upon extended reaction times.
• Biosynthesis of the thiamin pyrimidine: the reconstitution of a remarkable rearrangement reaction
  作者：Brian G. Lawhorn、Ryan A. Mehl、Tadhg P. Begley

  DOI：10.1039/b405429f

  日期：——

  The conversion of 5-aminoimidazole ribonucleotide (AIR) into 4-amino-2-methyl-5-hydroxymethylpyrimidine (HMP) is a fascinating reaction on the thiamin biosynthetic pathway in bacteria and is probably the most complex unresolved rearrangement in primary metabolism. We have successfully reconstituted this reaction in a cell-free system. The E. coli thiC gene product and an additional unidentified E. coli protein are required for the reaction. In addition, SAM and nicotinamide cofactors are required for full activity. Labeling studies to determine the origin of most of the atoms in the pyrimidine are described. Based on these studies, a new mechanism for HMP formation is proposed.

  5-氨基咪唑核苷酸（AIR）转化为4-氨基-2-甲基-5-羟甲基嘧啶（HMP）的反应是细菌硫胺素生物合成途径中的一个迷人反应，可能是初级代谢中最复杂的未解决重排反应。我们已经成功地在无细胞系统中重构了这个反应。E. coli 的 thiC 基因产物以及一个额外的未鉴定的 E. coli 蛋白质是反应所必需的。此外，SAM 和烟酰胺辅因子也是完全活性所需的。我们描述了标记研究，以确定嘧啶中大多数原子的来源。基于这些研究，提出了一种 HMP 形成的新机制。