3-deoxy-D-ribo-hexopyranose | 36204-29-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-deoxy-D-ribo-hexopyranose
• 英文别名: 3-deoxy-D-ribo-hexose；3-deoxy-D-glucose；D-ribo-3-deoxy-hexose；ξ-D-ribo-3-deoxy-hexopyranose；(3R,5S,6R)-6-(hydroxymethyl)tetrahydro-2H-pyran-2,3,5-triol；3-deoxy-D-glucopyranose；(3R,5S,6R)-6-(hydroxymethyl)oxane-2,3,5-triol
• CAS: 36204-29-2
• 化学式: C₆H₁₂O₅
• 分子量: 164.158
• InChiKey: RJDIFQMDPPUATQ-JMSAOHGTSA-N

物化性质

• 沸点：
  396.9±42.0 °C(Predicted)
• 密度：
  1.533±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  11
• 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：

  3-deoxy-D-ribo-hexopyranose 在 吡啶 、 4-二甲氨基吡啶 、 三乙基硼 、 三(三甲基硅基)硅烷 、 氢溴酸 、 sodium methylate 、 溶剂黄146 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 38.0h， 生成 1,5-anhydro-3-deoxy-D-glucitol
  参考文献：
  名称：

  1,5-脱水-d-果糖衍生物的合成及其炎性体抑制剂的评价

  摘要：

  几个1,5-脱水-的合成d -fructose（1,5- AF）衍生物的炎性进行评价抑制活性。近来，据报道1，5-AF抑制炎症小体，尽管活性低。我们着眼于2-酮形式的1,5-AF的水合，并推测这种水合是低活性的原因。因此，我们合成了一些1,5-AF衍生物，这些衍生物将无法形成二聚体构象，并且有望对炎症小体具有较高的活性，然后通过使用小鼠骨髓-核糖核酸评估它们对NLRP3炎症小体的抑制活性。衍生的巨噬细胞和人类THP-1细胞。结果，某些合成的2-酮形式的化合物对NLRP3炎性小体的抑制活性比1,5-AF高得多。

  DOI：

  10.1016/j.bmc.2017.11.041
• 作为产物：
  描述：

  3-deoxy-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside 在 硫酸 作用下， 以 水 为溶剂， 反应 2.5h， 生成 3-deoxy-D-ribo-hexopyranose
  参考文献：
  名称：

  Liemann, Susanne; Klaffke, Werner, Liebigs Annalen, 1995, # 10, p. 1779 - 1788

  摘要：

  DOI：

文献信息

• Enzymatic aldol reaction/isomerization as a route to unusual sugars
  作者：J.Robert Durrwachter、H.M. Sweers、K. Nozaki、Chi-Huey Wong

  DOI：10.1016/s0040-4039(00)84233-1

  日期：1986.1

  Utilizing fructose diphosphate aldolase and glucose isomerase as catalysts, 3-, 5, and 6-deoxy- and 6-0-methylhexoses have been synthesized from dihydroxyacetone phosphate or acetol phosphate and the corresponding hydroxypropionaldehydes.

  利用果糖二磷酸醛缩酶和葡萄糖异构酶作为催化剂，已经从磷酸二羟基丙酮或磷酸丙酮醇和相应的羟基丙醛合成了3-，5和6-脱氧-和6-0-甲基己糖。
• [EN] NEOGLYCORANDOMIZATION AND DIGITOXIN ANALOGS<br/>[FR] ALEATOIRISATION DES NEOGLYCOSIDES ET ANALOGUES DE LA DIGITOXINE
  申请人：WISCONSIN ALUMNI RES FOUND

  公开号：WO2006002381A1

  公开（公告）日：2006-01-05

  The present invention provides methods of producing libraries of compounds with enhanced desirable properties and diminished side effects as well as the compounds produced by the methods. In preferred embodiments, methods of the present invention use a universal chemical glycosylation method that employs reducing sugars and requires no protection or activation. In a preferred embodiment, the invention provides a library of neoglycoside digitoxin analogs that includes compounds with significantly enhanced cytotoxic potency toward human cancer cells and tumor-specificity, but are less potent Na+/K+-ATPase inhibitors in a human cell line than digitoxin.

  本发明提供了一种生产具有增强理想性能和减少副作用的化合物库的方法，以及通过这些方法生产的化合物。在优选实施例中，本发明的方法使用一种通用的化学糖基化方法，该方法采用还原糖，无需保护或激活。在优选实施例中，本发明提供了一种新糖苷地高辛类似物库，其中包括对人类癌细胞具有显著增强的细胞毒性活性和肿瘤特异性的化合物，但在人类细胞系中对Na+/K+-ATPase的抑制作用较地高辛要弱。
• Assessing the Optimal Deoxygenation Pattern of Dodecyl Glycosides for Antimicrobial Activity Against<i>Bacillus anthracis</i>
  作者：Catarina Dias、Alice Martins、Ana Pelerito、Maria C. Oliveira、Marialessandra Contino、Nicola A. Colabufo、Amélia P. Rauter

  DOI：10.1002/ejoc.201801764

  日期：2019.3.31

  against antibiotic resistance emergence relies on the development of alternative antibiotics. Approaches towards new dodecyl deoxy and dideoxy glycosides were devised and compounds tested over Bacillus spp. and Enterococcus faecalis. The 4,6‐dideoxygenation pattern gave the most active glycoside against all tested microbes.

  对抗抗生素耐药性的出现有赖于替代抗生素的开发。设计了新的十二烷基脱氧和双脱氧糖苷的方法，并通过芽孢杆菌（Bacillus spp）对化合物进行了测试。和粪肠球菌。4,6-去氧合模式对所有受试微生物的糖苷活性最高。
• Chemical mapping of the active site of the glucoamylase of<i>Aspergillus niger</i>
  作者：Raymond U. Lemieux、Ulrike Spohr、Mimi Bach、Dale R. Cameron、Monica M. Palcic、Torben P. Frandsen、Bjarne B. Stoffer、Birte Svensson

  DOI：10.1139/v96-036

  日期：1996.3.1

  A recently developed technique for the probing of the combining sites of lectins and antibodies, to establish the structure of the epitope that is involved in the binding of an oligosaccharide, is used to study the binding of methyl α-isomaltoside by the enzyme glucoamylase. The procedure involved the determination of the effects on the kinetics of hydrolysis of both monodeoxygenation and mono-O-methylation at each of the seven hydroxyl groups in order to gain an estimate of the differential changes in the free energies of activation, ΔΔG^≠. As expected, from previous publications, both deoxygenation and O-methylation of OH-4 (reducing unit), OH-4′, or OH-6′ strongly hindered hydrolysis, whereas the kinetics were virtually unaffected by either the substitutions at OH-2 or structural changes at C-1. The substitutions at OH-3 caused increases of 2.1 and 1.9 kcal/mol in the ΔΔG^≠. In contrast, whereas deoxygenation of either OH-2′ or OH-3′ caused much smaller (0.96 and 0.52 kcal/mol) increases in ΔΔG^≠, the mono-O-methylations resulted in severe steric hindrance to the formation of the activated complex. The relatively weak effects of deoxygenation suggest that the hydroxyl groups are replaced by water molecules and thereby participate in the binding by contributing effective complementarity. Methyl α-isomaltoside was docked into the combining site of the X-ray crystal structure at 2.4 Å resolution of the complex with the inhibitor acarbose. A fit free of steric interactions with the protein was found that has the methyl α-glucopyranoside unit in the normal⁴C₁conformation and the other glucose unit approaching a half-chair conformation with the interunit fragment defined by the torsion angles [Formula: see text] The model provides a network of hydrogen bonds that appears to well represent the activated complex formed by the glucoamylase with both maltose and isomaltose since the structures appear to provide a sound rationale for both the specificity and catalysis provided by the enzyme. Key words: monodeoxy and mono-O-methyl derivatives of methyl α-isomaltoside, enzyme binding domain, functioning of glucoamylase, differential changes in free energy of activation, characteristics of hydrogen bonding networks.

  最近开发的一种技术用于探测凝集素和抗体的结合位点，以建立与寡糖结合中涉及的表位的结构，用于研究酶葡萄糖酶对甲基α-异麦芽糖的结合。该过程涉及确定对水解动力学的影响，包括每个七个羟基的单去氧和单-O-甲基化，以获得活化自由能的差异变化ΔΔG^≠的估计。如预期的那样，根据先前的发表，OH-4（还原单元）、OH-4'或OH-6'的脱氧和O-甲基化强烈阻碍了水解，而OH-2的置换或C-1的结构变化几乎不影响动力学。OH-3的置换导致ΔΔG^≠增加了2.1和1.9 kcal/mol。相比之下，OH-2'或OH-3'的脱氧导致ΔΔG^≠增加较小（0.96和0.52 kcal/mol），而单-O-甲基化导致了对激活复合物形成的严重位阻。脱氧的相对较弱影响表明，羟基被水分子取代，从而通过提供有效的互补性参与结合。甲基α-异麦芽糖被对接到X射线晶体结构的结合位点，分辨率为2.4 Å的复合物与抑制剂阿卡波糖。找到了与蛋白质无位阻相互作用的适合，其中甲基α-葡萄糖吡喃糖单元处于正常的4C1构象，另一个葡萄糖单元接近半椅构象，其间单元片段由扭转角度定义[Formula: see text]该模型提供了一个氢键网络，似乎很好地代表了由葡萄糖酶与麦芽糖和异麦芽糖形成的激活复合物，因为这些结构似乎为酶提供的特异性和催化提供了合理的基础。关键词：甲基α-异麦芽糖的单去氧和单-O-甲基衍生物，酶结合结构域，葡萄糖酶的功能，活化自由能的差异变化，氢键网络的特性。
• Chemoenzymatic Synthesis of Trehalose Analogues: Rapid Access to Chemical Probes for Investigating Mycobacteria
  作者：Bailey L. Urbanek、Douglas C. Wing、Krystal S. Haislop、Chelsey J. Hamel、Rainer Kalscheuer、Peter J. Woodruff、Benjamin M. Swarts

  DOI：10.1002/cbic.201402288

  日期：2014.9.22

  Trehalose tools for TB: A one‐step chemoenzymatic method for the rapid and efficient synthesis of trehalose analogues was developed. This method enabled facile preparation and administration of a trehalose‐based probe for detecting mycobacteria, which might enable the development of new diagnostic tools for tuberculosis (TB) research.

  用于结核病的海藻糖工具：开发了一种用于快速有效合成海藻糖类似物的一步化学酶法。这种方法使得可以方便地制备和使用基于海藻糖的探针来检测分枝杆菌，这可能有助于开发用于结核病（TB）研究的新诊断工具。