(3R,4S,5R)-3,4-dihydroxy-5-(trityloxymethyl)-dihydrofuran-2(3H)-one | 84911-43-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (3R,4S,5R)-3,4-dihydroxy-5-(trityloxymethyl)-dihydrofuran-2(3H)-one
• 英文别名: 5-O-triphenylmethyl-D-ribono-γ-lactone；5-O-trityl-D-ribono-1,4-lactone；(+)-5-O-trityl-D-ribonolactone；5-O-(triphenylmethyl)-D-ribono-1,4-lactone；(3R,4S,5R)-3,4-dihydroxy-5-(trityloxymethyl)oxolan-2-one
• CAS: 84911-43-3
• 化学式: C₂₄H₂₂O₅
• 分子量: 390.436
• InChiKey: SEMNSEULNGXIGD-YPAWHYETSA-N

物化性质

• 熔点：
  104.6 °C
• 沸点：
  546.8±19.0 °C(Predicted)
• 密度：
  1.293±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R,4S,5R)-3,4-dihydroxy-5-(trityloxymethyl)-dihydrofuran-2(3H)-one 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 5-O-trityl-D-ribitol
  参考文献：
  名称：

  Yarrowia lipolytica dehydrogenase/reductase: An enzyme tolerant for lipophilic compounds and carbohydrate substrates

  摘要：

  Yarrowia lipolytica short chain dehydrogenase/reductase (YlSDR) was expressed in Escherichia coli, purified and characterized in vitro. The substrate scope for YlSDR mediated oxidation was investigated with alcohols and unprotected carbohydrates spectrophotometrically, revealing a preference for secondary compared to primary alcohols. In reduction direction, YlSDR was highly active on ribulose and fructose, suggesting that the enzyme is a mannitol-2-dehydrogenase. In order to explore substrate tolerance especially for space-demanding, lipophilic protecting groups, 5-O-trityl-D-ribitol and 5-O-trityl-alpha,beta-D-ribose were investigated as substrates: YlSDR oxidized 5-O-trityl-D-ribitol and 5-O-trityl-alpha,beta-D-ribose and reduced the latter at the expense of NADP(H). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.064
• 作为产物：
  描述：

  5-O-三苯甲基-D-呋喃核糖 在 溴 、 barium carbonate 作用下， 以 水 为溶剂， 以45%的产率得到(3R,4S,5R)-3,4-dihydroxy-5-(trityloxymethyl)-dihydrofuran-2(3H)-one
  参考文献：
  名称：

  Yarrowia lipolytica dehydrogenase/reductase: An enzyme tolerant for lipophilic compounds and carbohydrate substrates

  摘要：

  Yarrowia lipolytica short chain dehydrogenase/reductase (YlSDR) was expressed in Escherichia coli, purified and characterized in vitro. The substrate scope for YlSDR mediated oxidation was investigated with alcohols and unprotected carbohydrates spectrophotometrically, revealing a preference for secondary compared to primary alcohols. In reduction direction, YlSDR was highly active on ribulose and fructose, suggesting that the enzyme is a mannitol-2-dehydrogenase. In order to explore substrate tolerance especially for space-demanding, lipophilic protecting groups, 5-O-trityl-D-ribitol and 5-O-trityl-alpha,beta-D-ribose were investigated as substrates: YlSDR oxidized 5-O-trityl-D-ribitol and 5-O-trityl-alpha,beta-D-ribose and reduced the latter at the expense of NADP(H). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.064

文献信息

• Monitoring Poly(ADP-ribosyl)glycohydrolase Activity with a Continuous Fluorescent Substrate
  作者：Bryon S. Drown、Tomohiro Shirai、Johannes Gregor Matthias Rack、Ivan Ahel、Paul J. Hergenrother

  DOI：10.1016/j.chembiol.2018.09.008

  日期：2018.12

  monomers from their protein targets. Existing methods for monitoring these hydrolases rely on detection of the natural substrate, PAR, commonly achieved via radioisotopic labeling. Here we disclose a general substrate for monitoring PARG activity, TFMU-ADPr, which directly reports on total PAR hydrolase activity via release of a fluorophore; this substrate has excellent reactivity, generality (processed by

  翻译后修饰（PTM）和信号分子聚（ADP-核糖）（PAR）对多种生物过程都有影响。此PTM受一系列ADP-核糖基糖水解酶（PARG酶）调控，该酶可将聚合物裂解和/或将单体从其蛋白质靶标中释放出来。监测这些水解酶的现有方法依赖于通常通过放射性同位素标记实现的天然底物PAR的检测。在这里，我们公开了用于监测PARG活性的通用底物TFMU-ADPr，其通过荧光团的释放直接报告总PAR水解酶活性。这种底物具有出色的反应性，通用性（由主要的PARG酶处理），稳定性和可用性。第二种底物TFMU-IDPr仅从酶ARH3选择性报告PARG活性。在全细胞裂解物实验中使用这些探针揭示了霍乱毒素可抑制ARH3的机制。TFMU-ADPr和TFMU-IDPr是用于评估体外小分子抑制剂和探索ADP-核糖基分解代谢酶调控的多功能工具。
• [EN] FLUORESCENT SUBSTRATES FOR POLY(ADP-RIBOSYL) HYDROLASES<br/>[FR] SUBSTRATS FLUORESCENTS POUR POLY(ADP-RIBOSYL) HYDROLASES
  申请人：UNIV ILLINOIS

  公开号：WO2020055753A1

  公开（公告）日：2020-03-19

  The post-translational modification (PTM) and signaling molecule poly(ADP-ribose) (PAR) has an impact on diverse biological processes. PTM is regulated by a series of ADP-ribosyl glycohydrolases (PARG enzymes) that cleave polymers and/or liberate monomers from their protein targets. Disclosed herein is a substrate for monitoring PARG activity, TFMU-ADPr, which directly reports on total PAR hydrolase activity via release of a fluorophore; this substrate has excellent reactivity, generality, stability, and usability. A second substrate, TFMU-IDPr, selectively reports on PARG activity only from the enzyme ARH3. Use of these probes in whole-cell lysate experiments has revealed a mechanism by which ARH3 is inhibited by cholera toxin. TFMU-ADPr and TFMU-IDPr are versatile tools for assessing small-molecule inhibitors in vitro and probing the regulation of ADP-ribosyl catabolic enzymes.

  翻译结果：翻译后修饰（PTM）和信号分子聚腺苷二磷酸核糖（PAR）对多种生物过程产生影响。PTM受一系列ADP核糖水解酶（PARG酶）调控，这些酶从它们的蛋白靶标中切割聚合物和/或释放单体。本文披露了一种用于监测PARG活性的底物，TFMU-ADPr，它通过释放荧光团直接报告总PAR水解酶活性；该底物具有出色的反应性、普适性、稳定性和可用性。第二种底物TFMU-IDPr，只选择性地报告来自酶ARH3的PARG活性。在全细胞裂解液实验中使用这些探针揭示了一种由霍乱毒素抑制ARH3的机制。TFMU-ADPr和TFMU-IDPr是评估体外小分子抑制剂和探究ADP核糖降解酶调控的多功能工具。
• Studies on structurally simple α,β-butenolides—II
  作者：P. Camps、J. Cardellach、J. Font、R.M. Ortuño、O. Ponsati

  DOI：10.1016/0040-4020(82)87017-8

  日期：1982.1

  A short synthesis of the title compound, 16, from d-ribonolactone is described. Two alternative approaches differing in the timing of the CC double bond creation are used to prepare some chiral derivatives of 16. (−)-Ranunculin, a glycoside present in Ranunculaceae, has been synthesized for the first time.

  描述了由d-核糖内酯简短合成标题化合物16。在C alternativeC双键产生时间上有两种不同的替代方法，用于制备一些16的手性衍生物。（ - ） - Ranunculin，糖苷存在于毛茛科，已合成的第一次。
• Synthesis of 5-deoxy-5-phospho-d-ribonohydroxamic acid: a new competitive and selective inhibitor of type B ribose-5-phosphate isomerase from Mycobacterium tuberculosis
  作者：Emmanuel Burgos、Annette K. Roos、Sherry L. Mowbray、Laurent Salmon

  DOI：10.1016/j.tetlet.2005.03.151

  日期：2005.5

  the allose-6-phosphate isomerase reaction, was obtained by a six-step synthesis from d-erythronolactone. In contrast to the known competitive ribose-5-phosphate isomerase (Rpi) inhibitors 4-deoxy-4-phospho-d-erythronohydroxamic acid, 4-deoxy-4-phospho-d-erythronate, and 4-deoxy-4-phosphonomethyl-d-erythronate, the new hydroxamic acid selectively inhibits Mycobacterium tuberculosis RpiB (Ki = 0.40 mM,

  5-脱氧-5-磷酸-d-核糖基异羟肟酸是通过6步合成的d-磷酸-异戊糖-6-磷酸异构酶反应的1,2-顺式-烯二醇酯高能中间物种的模拟物。赤藓内酯。与已知的竞争性核糖5-磷酸异构酶（Rpi）抑制剂相反，4-脱氧-4-磷酸-d-赤藓酸异羟肟酸，4-脱氧-4-磷酸-d-赤藓酸，和4-脱氧-4-膦酰基甲基- d-赤藓酸酯，新的异羟肟酸 相对于菠菜有选择性地抑制结核分枝杆菌RpiB（K i  = 0.40 mM，K m / K i = 4.5） RpiA，因此似乎是设计有效的细菌酶物种特异性抑制剂的有希望的先导。
• A synthetic route to 3-C-alkyl (or 3-C-phenyl-) 2,3-dideoxy-d-erythro-pentono-1,4-lactones: intermediates in the synthesis of 2(3H)-furanones
  作者：Panolil C. Raveendranath、Vincent J. Blazis、Kwasi Agyei-Aye、Anna K. Hebbler、Lisa N. Gentile、Elma S. Hawkins、Stephen C. Johnson、David C. Baker

  DOI：10.1016/0008-6215(94)80066-9

  日期：1994.2

  A series of 3-C-alkyl- (and 3-C-phenyl-) 2,3-dideoxy-D-erythro-pentono-1,4-lactones, compounds which are important in the synthesis of modified nucleosides and antibiotic sugars, were synthesized from D-ribonolactone. By a route that proceeded via 5-O-protected D-ribonolactone, 5-O-protected 2,3-dideoxy-D-glycero-pent-2-enono-1,4-lactones were synthesized and reacted with R2CuLi or a complex PhSCu(RMgBr)n

  一系列3-C-烷基-（和3-C-苯基-）2，3-二脱氧-D-赤-戊基-1，4-内酯，这些化合物在合成修饰的核苷和抗生素糖中很重要，由D-核糖内酯合成。通过经由5-O-保护的D-核糖内酯进行的途径，合成了5-O-保护的2,3-二脱氧-D-甘油-戊-2-enono-1,4-内酯，并与R2CuLi或络合物反应用PhSCu（RMgBr）n分别得到3-C-烷基或3-C-苯基化合物。提供了O-保护的中间体的制备以及有机金属试剂的选择的细节。