[1-2H]-D-ribose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [1-2H]-D-ribose
• 英文别名: (3R,4S,5R)-2-deuterio-5-(hydroxymethyl)oxolane-2,3,4-triol
• 化学式: C₅H₁₀O₅
• 分子量: 151.123
• InChiKey: HMFHBZSHGGEWLO-ROIYBNBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  10
• 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：
  90.2
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [1-2H]-D-ribose 在 吡啶 、 硫酸 作用下， 以 溶剂黄146 为溶剂， 生成 1,2,3,5-tetra-O-acetyl-1-deutero-D-ribofuranose
  参考文献：
  名称：

  Baker, Stephen J.; Young, Douglas W., Journal of labelled compounds and radiopharmaceuticals, 2000, vol. 43, # 10, p. 1022 - 1032

  摘要：

  DOI：
• 作为产物：
  描述：

  D-(+)-核糖酸-1,4-内酯 在 sodium amalgam 、 重水 作用下， 以89%的产率得到[1-2H]-D-ribose
  参考文献：
  名称：

  用于研究DNA和RNA的特殊氘代核苷酸的一般合成。

  摘要：

  描述了用于制备在1'，4'或5'位置掺入氘的核糖核苷酸和脱氧核糖核苷酸的有效方法。通过化学合成制备了三种中间体-[1-2H] -D-核糖，[4-2H] -D-核糖和[5-2H（2）]-D-核糖，随后通过以下方法转化为核糖核苷酸和脱氧核糖核苷酸酶促反应。获得毫克量的所需产物，平均氘含量为96 +/- 1％。

  DOI：

  10.1016/s0960-894x(02)00650-9

文献信息

• Preparation of 1'-C Deuterated Synthons for RNA Synthesis by H-Phosphonate Method Aiming at Two-Dimensional NMR Secondary Structure Studies
  作者：Luboš Arnold、Martina Pressová、David Šaman、Martin Vogtherr、Stefan Limmer

  DOI：10.1135/cccc19960389

  日期：——

  1'-C Deuterated H-phosphonate synthons were prepared via a 12-step procedure starting from [1'-²H]ribose. The procedure included nucleosidation of 1'-O-acetyl-2',3',5'-O-tribenzoyl[1'-²H]ribose with appropriately protected nucleobases and preparation of nucleoside-H-phosphonates by slightly modified described procedures. The automated RNA synthesis of 5'-G^*C^*U^*A^*U^*UUAU-3' and 3'-AC^*G^*A^*U^*A^*AAGU-5' was performed on a Gene Assembler Plus DNA-synthesizer. These specifically deuterated oligoribonucleotides were subsequently compared with the corresponding non-deuterated sequences using 2D-NMR NOESY spectra. Specific deuterium incorporation resulted in the expected simplification of spectral pattern.

  通过一个12步的程序，从[1'-2H]核糖开始制备了1'-C氘代H-膦酸酯合成单体。该程序包括将1'-O-乙酰-2',3',5'-O-三苯甲酰[1'-2H]核糖与适当保护的核碱基进行核苷化，以及通过略微修改的描述程序制备核苷-H-膦酸酯。在Gene Assembler Plus DNA合成仪上进行了5'-G*C*U*A*U*UUAU-3'和3'-AC*G*A*U*A*AAGU-5'的自动RNA合成。随后，将这些特异氘代寡核糖核苷酸与相应的非氘代序列进行比较，使用2D-NMR NOESY谱。特定氘的加入导致了谱图的预期简化。
• A general synthesis of specifically deuterated nucleotides for studies of DNA and RNA
  作者：Bingzi Chen、Elizabeth R. Jamieson、Thomas D. Tullius

  DOI：10.1016/s0960-894x(02)00650-9

  日期：2002.11

  ribonucleotides and deoxyribonucleotides with deuterium incorporated at the 1', 4', or 5' position. Three intermediates-[1-2H]-D-ribose, [4-2H]-D-ribose, and [5-2H(2)]-D-ribose-were prepared by chemical synthesis and subsequently converted to ribonucleotides and deoxyribonucleotides via enzymatic reactions. Milligram quantities of the desired products were obtained with an average deuterium content of 96+/-1%

  描述了用于制备在1'，4'或5'位置掺入氘的核糖核苷酸和脱氧核糖核苷酸的有效方法。通过化学合成制备了三种中间体-[1-2H] -D-核糖，[4-2H] -D-核糖和[5-2H（2）]-D-核糖，随后通过以下方法转化为核糖核苷酸和脱氧核糖核苷酸酶促反应。获得毫克量的所需产物，平均氘含量为96 +/- 1％。
• 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。
• A “Radical Dance” in Thiamin Biosynthesis: Mechanistic Analysis of the Bacterial Hydroxymethylpyrimidine Phosphate Synthase
  作者：Abhishek Chatterjee、Amrita B. Hazra、Sameh Abdelwahed、David G. Hilmey、Tadhg P. Begley

  DOI：10.1002/anie.201003419

  日期：2010.11.8

  Tricky things with ThiC: Hydroxymethylpyrimidine phosphate (HMP‐P) synthase (ThiC) catalyzes one of the most complex rearrangement reactions in primary metabolism. Deuteration experiments show that under reducing conditions, in the presence of aminoimidazole ribonucleotide, the 5′‐deoxyadenosyl radical generated at the active site of ThiC reacts directly with the substrate and performs two iterative

  ThiC 的棘手问题：羟甲基嘧啶磷酸 (HMP-P) 合酶 (ThiC) 催化初级代谢中最复杂的重排反应之一。氘化实验表明，在还原条件下，在氨基咪唑核糖核苷酸的存在下，在 ThiC 活性位点产生的 5'-脱氧腺苷自由基直接与底物反应并进行两次迭代氢原子提取事件以催化这种重排（参见方案；SAM = S-腺苷甲硫氨酸）。
• <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.