D-[1-13C]ribose | 70849-24-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: D-[1-13C]ribose
• 英文别名: D-ribose-1-¹³C；(3R,4S,5R)-5-(Hydroxymethyl)(213C)oxolane-2,3,4-triol
• CAS: 70849-24-0
• 化学式: C₅H₁₀O₅
• 分子量: 151.12
• InChiKey: HMFHBZSHGGEWLO-LZOXQHQWSA-N

物化性质

• 熔点：
  94 °C (dec.)(lit.)
• 溶解度：
  甲醇（微溶）、水（微溶）

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

制备方法与用途

D-核糖（标记为D-Ribose-13C）是一种含有13C的D-核糖。作为一种能量增强剂，D-核糖作为ATP的糖成分被广泛用作慢性疲劳综合征或心脏能量代谢的代谢治疗补充。它在蛋白质糖基化过程中也具有活性。

反应信息

• 作为反应物：
  描述：

  D-[1-13C]ribose 在 吡啶 、 三氟甲磺酸三甲基硅酯 、 硫酸 、 氨 、 溶剂黄146 、 六甲基二硅氮烷 作用下， 以 氯仿 为溶剂， 反应 50.0h， 生成 [1'-13C]尿苷
  参考文献：
  名称：

  13C-Enriched ribonucleosides：合成和应用 13C-1H 和 13C-13C 自旋耦合常数来评估呋喃糖和 N-糖苷键构象

  摘要：

  腺苷 (1)、胞苷 (2)、鸟苷 (3) 和尿苷 (4) 已通过化学方法制备，在核糖环的 C1{prime} 和 C2{prime} 处 {sup 13}C 富集（99 原子%） . 已开发出可靠的合成方案，以允许获得稳定同位素标记寡核苷酸的结构研究和体内代谢研究所需的毫摩尔数量的标记核糖核苷。获得了富集核糖核苷的高分辨率{sup 1}H和{sup 13}C NMR谱，{sup 13}C-{sup 13}C和{sup 13}C-{sup 1}H自旋-已经测量了{β}-D-呋喃核糖环内和穿过N-糖苷键的途径的偶联常数。在甲基 {α}- 和 {β}-D-核硼苷 (5,6) 以及两种构象受限的核苷 2 中确定了相关偶联，2{prime}-anhydro-(1-{beta}-D-arabinofuranosyl)uracil (7) 和 2{prime},3{prime}-O-isopropylidene-2

  DOI：

  10.1021/ja00176a043

文献信息

• The nucleoside transport proteins, NupC and NupG, from Escherichia coli: specific structural motifs necessary for the binding of ligands
  作者：Simon G. Patching、Stephen A. Baldwin、Alexander D. Baldwin、James D. Young、Maurice P. Gallagher、Peter J. F. Henderson、Richard B. Herbert

  DOI：10.1039/b414739a

  日期：——

  unrelated transporters showed similar but distinct patterns of inhibition, revealing differing selectivities for the different nucleosides and their analogues. Binding of nucleosides to NupG required the presence of hydroxyl groups at each of the C-3' and C-5' positions of ribose, while binding to NupC required only the C-3' hydroxyl substituent. The greater importance of the ribose moiety for binding to

  测试了一系列46种天然核苷和类似物（主要是基于腺苷的）作为从大肠杆菌中富集的，与H（+）连接的核苷转运蛋白NupC和NupG吸收[U-（14）C]尿苷的抑制剂。这两个在进化上不相关的转运蛋白显示出相似但不同的抑制模式，揭示了对不同核苷及其类似物的不同选择性。核苷与NupG的结合需要在核糖的C-3'和C-5'位置分别存在羟基，而与NupC的结合仅需要C-3'羟基取代基。核糖部分对于结合NupG的重要性更高，与该蛋白质和寡糖之间的进化关系一致：运输者的主要促进者超家族（MFS）的H（+）同向转运蛋白（OHS）亚家族。对于两种蛋白质，C-3'处的天然α-构型和C-1'处的天然β-构型对于配体结合都是必需的。发现腺苷的咪唑环中的N-7和C-6的氨基对于结合并不重要，并且两个转运蛋白都显示出C-6 / N取代的灵活性。N-1和N-3中的一个或两个对腺苷类似物与NupC的结合很重要，但对NupG的结合
• EFFICIENT SYNTHESIS OF<scp>D</scp>-[1′-¹³C]-RIBONUCLEOSIDES FOR INCORPORATION INTO OLIGO-RNA
  作者：Y. Saito、A. Nyilas、L. A. Agrofoglio

  DOI：10.1081/ncn-100002463

  日期：2001.3.31

  Syntheses of the monomer building blocks used for the solid-phase synthesis of specifically 1'-13C-labeled oligoribonucleotides from the D-[1-13C]ribose is presented. Procedure has been used for the selective formation of 2'-O-silylated ribonucleosides. After 5'-O-dimethoxytritylation, the synthesis of D-[1'-13C] ribonucleoside phosphoramidites has been achieved.

  提出了用于从D- [1-13C]核糖固相合成特定的1'-13C标记的寡核糖核苷酸的单体结构单元的合成。该方法已用于选择性形成2'-O-甲硅烷基化的核糖核苷。在5'-O-二甲氧基三苯甲基化之后，已经实现了D- [1'-13C]核糖核苷亚磷酰胺的合成。
• Mechanistic Insight into the Origin of Stereoselectivity in the Ribose-Mediated Strecker Synthesis of Alanine
  作者：Luca Legnani、Andrea Darù、Alexander X. Jones、Donna G. Blackmond

  DOI：10.1021/jacs.1c03552

  日期：2021.5.26

  mediated by chiral pentose sugars. Experimental kinetic and spectroscopic results combined with DFT computational studies and microkinetic modeling help to identify the nature of the intermediate species and provide insight into the stereoselectivity of their hydrolysis in the prebiotically relevant ribose–alanine system. These studies support a synergistic role for sugars and amino acids in the emergence

  对映体富集的氨基酸是在由手性戊糖介导的外消旋氨基腈的水解动力学拆分中产生的。实验动力学和光谱结果与 DFT 计算研究和微动力学模型相结合，有助于确定中间体的性质，并深入了解它们在益生元相关核糖-丙氨酸系统中水解的立体选择性。这些研究支持糖和氨基酸在生物分子同手性出现中的协同作用。
• 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）。
• Synthesis of Carbohydrates in Mineral-Guided Prebiotic Cycles
  作者：Hyo-Joong Kim、Alonso Ricardo、Heshan I. Illangkoon、Myong Jung Kim、Matthew A. Carrigan、Fabianne Frye、Steven A. Benner

  DOI：10.1021/ja201769f

  日期：2011.6.22

  One present obstacle to the "RNA-first" model for the origin of life is an inability to generate reasonable "hands off" scenarios for the formation of carbohydrates under conditions where they might have survived for reasonable times once formed. Such scenarios would be especially compelling if they deliver pent(ul)oses, five-carbon sugars found in terran genetics, and exclude other carbohydrates (e.g., aldotetroses) that may also be able to function in genetic systems. Here, we provide detailed chemical analyses of carbohydrate premetabolisin, showing how borate, molybdate, and calcium minerals guide the formation of tetroses (C(4)H(8)O(4)), heptoses (C(7)H(14),O(7)), and pentoses (C(5)H(10)O(5)), including the ribose found in RNA, in "hands off" experiments, starting with formaldehyde and glycoaldehyde. These results show that pent(ul)oses would almost certainly have formed as stable borate complexes on the surface of an early Earth beneath a humid CO(2) atmosphere suffering electrical discharge. While aldotetroses form extremely stable complexes with borate, they are not accessible by pathways plausible under the most likely early Earth scenarios. The stabilization by borate is not, however, absolute. Over longer times, material is expected to have passed from borate-bound pent(ul)oses to a branched heptulose, which is susceptible to Cannizzaro reduction to give dead end products. We show how this fate might be avoided using molybdate-catalyzed rearrangement of a branched pentose that is central to borate-moderated cycles that fix carbon from formaldehyde. Our emerging understanding of the nature of the early Earth, including the presence of hydrated rocks undergoing subduction to form felsic magmas in the early Hadean eon, may have made borate and molydate species available to prebiotic chemistry, despite the overall "reduced" state of the planet.