(3R,4S,5R)-5-(azidomethyl)tetrahydrofuran-2,3,4-triol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,4S,5R)-5-(azidomethyl)tetrahydrofuran-2,3,4-triol
• 英文别名: 5-azidoribose；(3R,4S,5R)-5-(azidomethyl)oxolane-2,3,4-triol
• 化学式: C₅H₉N₃O₄
• 分子量: 175.144
• InChiKey: FPNYNARZVKFPAC-SOOFDHNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  84.3
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3R,4S,5R)-5-(azidomethyl)tetrahydrofuran-2,3,4-triol 在 palladium on activated charcoal 氢气 、 溴 、 barium carbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 生成 (3R,4R,5R)-3,4,5-trihydroxypiperidin-2-one
  参考文献：
  名称：

  Synthesis of 5-Amino-5-deoxypentonolactams

  摘要：

  从D-木糖和D-阿拉伯糖开始制备5-Azido-5-deoxy-1,2-O-异丙基亚-α-D-木糖呋喃糖（4）和5-azido-5-deoxy-1,2-O-异丙基亚-β-D-阿拉伯呋喃糖（10）。使用氧化还原法进行C-3异构化，从4和10分别得到5-azido-5-deoxy-1,2-O-异丙基亚-α-D-核糖呋喃糖（15）和5-azido-5-deoxy-1,2-O-异丙基亚-β-D-莱克索呋喃糖（17）。通过酸水解、溴氧化和催化氢化，分别得到相应的5-azido-5-deoxy-D-戊糖呋喃糖6、11、18、19，5-azido-5-deoxy-D-戊内酯7、12、20、21和5-氨基-5-deoxy-D-戊内酰胺8、13、22、23。

  DOI：

  10.1135/cccc19961027
• 作为产物：
  描述：

  methyl 5-azido-5-deoxy-2,3-O-isopropylidene-b-ribofuranoside 在 硫酸 作用下， 反应 4.0h， 生成 (3R,4S,5R)-5-(azidomethyl)tetrahydrofuran-2,3,4-triol
  参考文献：
  名称：

  Chemical investigations in the synthesis of O-serinyl aminoribosides

  摘要：

  Glycosylation involving D-ribose derivatives and various N-protected tert-butyl L-serinates can be achieved efficiently by careful choice of the activation method at the anomeric position and of the Lewis acid promoter. The conditions described allow the major formation of the P-anomer required for further elaboration to liposidomycin and caprazamycin analogues. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.11.019

文献信息

• Adenosine Kinase Inhibitors. 1. Synthesis, Enzyme Inhibition, and Antiseizure Activity of 5-Iodotubercidin Analogues
  作者：Bheemarao G. Ugarkar、Jay M. DaRe、Joseph J. Kopcho、Clinton E. Browne、Juergen M. Schanzer、James B. Wiesner、Mark D. Erion

  DOI：10.1021/jm000024g

  日期：2000.7.1

  side effects. Adenosine kinase inhibitors (AKIs) represent an alternative strategy, since AKIs may raise local adenosine levels in a more site- and event-specific manner and thereby elicit the desired pharmacology with a greater therapeutic window. Starting with 5-iodotubercidin (IC50 = 0.026 microM) and 5'-amino-5'-deoxyadenosine (IC50 = 0.17 microM) as lead inhibitors of the isolated human AK, a variety

  腺苷受体激动剂产生多种治疗上有用的药理学。然而，迄今为止，由于剂量限制的副作用，它们未能成功进行临床开发。腺苷激酶抑制剂（AKIs）代表了另一种策略，因为AKIs可以以更多位点和事件特异性的方式提高局部腺苷水平，从而以更大的治疗窗口引发所需的药理作用。从5-碘代小球蛋白（IC50 = 0.026 microM）和5'-氨基-5'-脱氧腺苷（IC50 = 0.17 microM）作为分离的人AK的主要抑制剂开始，各种吡咯并[2,3-d]嘧啶核苷类似物通过使用钠盐介导的糖基化方法将5-取代的4-取代的4-氯吡咯并[2,3-d]嘧啶碱基与核糖类似物偶联来设计和制备。5'-氨基-5' 发现5-溴和5-碘结核菌素的β-脱氧类似物是迄今为止报道的最有效的AKI（IC50S <0.001 microM）。在大鼠最大电击（MES）诱发的癫痫发作试验中，几种有效的AKIs表现出抗惊厥活性。
• An Azidoribose Probe to Track Ketoamine Adducts in Histone Ribose Glycation
  作者：Igor Maksimovic、Qingfei Zheng、Marissa N. Trujillo、James J. Galligan、Yael David

  DOI：10.1021/jacs.0c01325

  日期：2020.6.3

  physiological importance requires specific chemical tools. Here we present the novel chemoenzymatic syntheses of an active azido-modified ribose analog, 5-azidoribose (5-AR), as well as an inactive control derivative, 1-azidoribose (1-AR) and their application towards understanding protein ribose-glycation in vitro and in cellulo. With these new probes we found that, similar to MGO-glycation, ribose glycation

  反应性细胞代谢物可以修饰大分子并形成加合物，称为非酶共价修饰 (NECM)。由于所形成的加合物的性质复杂且常常不明确，剖析 NECM（例如糖化）的机制、调节和后果一直具有挑战性。直接追踪关键靶标修饰的形成以揭示其潜在的生理重要性需要特定的化学工具。在这里，我们介绍活性叠氮基修饰核糖类似物 5-叠氮核糖 (5-AR) 以及无活性对照衍生物 1-叠氮核糖 (1-AR) 的新型化学酶合成方法及其在理解蛋白质核糖糖化方面的应用体外和纤维素中。通过这些新探针，我们发现，与 MGO 糖化类似，核糖糖化特异性地积聚在组蛋白上。除了荧光标记之外，我们还展示了探针在富集修饰靶标方面的实用性，这些靶标是通过无标记定量蛋白质组学和高分辨率 MS/MS 工作流程进行识别的。最后，我们确定已知的癌蛋白和己糖脱糖酶、果糖胺 3-激酶 (FN3K) 能够识别并促进活细胞中 5-AR 糖基化加合物的去除，支持核糖糖基化的动态调节，并验证探针作为监测
• Glucose isomerase catalysed isomerisation reactions of (2R,3R)-configured aldofuranoses into the corresponding open-chain 2-ketoses
  作者：Michael Ebner、Arnold E. Stütz

  DOI：10.1016/s0008-6215(97)00206-1

  日期：1997.12

  Immobilised glucose isomerase (EC 5.3.1.5) accepted various (2R,3R)-configured aldofuranoses such as D-erythrose, as well as homologous C-5-modified D-ribose derivatives, as substrates. In the case of D-erythrose, quantitative conversion into D-glycero-tetrulose took place. D-Ribofuranoses were converted into the corresponding open-chain 2-ketoses in isolated yields of 65%. Surprisingly, L-erythrose also turned out to be a substrate of this enzyme. (C) 1998 Elsevier Science Ltd.
• Chemical investigations in the synthesis of O-serinyl aminoribosides
  作者：Maryon Ginisty、Christine Gravier-Pelletier、Yves Le Merrer

  DOI：10.1016/j.tetasy.2005.11.019

  日期：2006.1

  Glycosylation involving D-ribose derivatives and various N-protected tert-butyl L-serinates can be achieved efficiently by careful choice of the activation method at the anomeric position and of the Lewis acid promoter. The conditions described allow the major formation of the P-anomer required for further elaboration to liposidomycin and caprazamycin analogues. (c) 2005 Elsevier Ltd. All rights reserved.
• Synthesis of 5-Amino-5-deoxypentonolactams
  作者：Karel Kefurt、Zdeňka Kefurtová、Věra Marková、Karla Slívová

  DOI：10.1135/cccc19961027

  日期：——

  5-Azido-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranose (4) and 5-azido-5-deoxy-1,2-O-isopropylidene-β-D-arabinofuranose (10) were prepared starting from D-xylose and D-arabinose, respectively. Using the oxidation-reduction way for the C-3 epimerization, 5-azido-5-deoxy-1,2-O-isopropylidene-α-D-ribofuranose (15) and 5-azido-5-deoxy-1,2-O-isopropylidene-β-D-lyxofuranose (17) were obtained from 4 and 10, respectively. The derivatives 4, 10, 15 and 17 afforded by acid hydrolysis, oxidation with bromine and catalytic hydrogenation successively the corresponding 5-azido-5-deoxy-D-pentofuranoses 6, 11, 18, 19, 5-azido-5-deoxy-D-pentonolactones 7, 12, 20, 21 and 5-amino-5-deoxy-D-pentonolactams 8, 13, 22, 23.

  从D-木糖和D-阿拉伯糖开始制备5-Azido-5-deoxy-1,2-O-异丙基亚-α-D-木糖呋喃糖（4）和5-azido-5-deoxy-1,2-O-异丙基亚-β-D-阿拉伯呋喃糖（10）。使用氧化还原法进行C-3异构化，从4和10分别得到5-azido-5-deoxy-1,2-O-异丙基亚-α-D-核糖呋喃糖（15）和5-azido-5-deoxy-1,2-O-异丙基亚-β-D-莱克索呋喃糖（17）。通过酸水解、溴氧化和催化氢化，分别得到相应的5-azido-5-deoxy-D-戊糖呋喃糖6、11、18、19，5-azido-5-deoxy-D-戊内酯7、12、20、21和5-氨基-5-deoxy-D-戊内酰胺8、13、22、23。