2,2',3,3',4,4',6-hepta-O-benzyl-α-D-trehalose | 103128-35-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2',3,3',4,4',6-hepta-O-benzyl-α-D-trehalose
• 英文别名: 2,3,4,2’,3’,4’,6’-hepta-O-benzyl-α,α’-trehalose；2,3,4,6,2',3',4'-hepta-O-benzyl-α,α-D-trehalose；2,3,4,2',3',4',6'-hepta-O-benzyl-α,α-D-trehalose；2,3,4,2',3',4',6'-Hepta-O-benzyl-alpha,alpha-D-trehalose；[(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-[(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyoxan-2-yl]methanol
• CAS: 103128-35-4
• 化学式: C₆₁H₆₄O₁₁
• 分子量: 973.173
• InChiKey: UQKLIZVLBDIVKJ-QHXLLDNWSA-N

物化性质

• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  72
• 可旋转键数：
  25
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2,2',3,3',4,4',6-hepta-O-benzyl-α-D-trehalose 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.33h， 以62%的产率得到2,2',3,3',4,4',6'-hepta-O-benzyl-6-carbaldehyde-α-D-glucopyranosyl-(1→1)-α-D-glucopyranoside
  参考文献：
  名称：

  基于海藻糖的分枝杆菌海藻糖 6-磷酸磷酸酶抑制剂的合成和体外表征。

  摘要：

  α,α'-海藻糖在参与致病性分枝杆菌毒力的几种细胞壁成分的合成中发挥作用。它在哺乳动物生物化学中的缺失使得海藻糖相关的生化过程成为化疗的潜在目标。海藻糖6-磷酸合成酶(TPS)/海藻糖6-磷酸磷酸酶(TPP)途径，也称为OtsA/OtsB2途径，是结核分枝杆菌(Mtb)中参与海藻糖生产的主要途径。此外，TPP 对于 Mtb 的生存至关重要。我们描述了 6-膦酸 4 (TMP)、6-亚甲基膦酸 5 (TEP) 和 6-N-膦酰胺 6 (TNP) 形式的 α,α'-海藻糖衍生物的合成。这些不可水解的 TPP 底物类似物作为 Mtb、慢黄分枝杆菌 (Mlt) 和三联分枝杆菌 (Mtx) TPP 的抑制剂进行了检查。在所有情况下，这些化合物在抑制 Mtx TPP 方面最有效，其中 TMP [IC50 =(288±32) μm] 作用最强，其次是 TNP [IC50 =(421±24) μm] 和 TEP

  DOI：

  10.1002/cbic.201800551
• 作为产物：
  描述：

  6-O-diphenoxyphosphoryl-2,3,4,2’,3’,4’,6’-hepta-O-benzyl-α,α’-trehalose 在 sodium nitrite 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以75%的产率得到2,2',3,3',4,4',6-hepta-O-benzyl-α-D-trehalose
  参考文献：
  名称：

  Simple one-pot regioselective 6-O-phosphorylation of carbohydrates and trehalose desymmetrization

  摘要：

  生物学上必需的碳水化合物6-磷酸，特别是海藻糖6-磷酸，可以通过涉及最少保护基团操作的两步反应，在优异的整体产率下轻松合成。我们可以裂解二苯基磷酸酯基团以实现进一步的合成目标。

  DOI：

  10.1039/c3cc47180b

文献信息

• [EN] DETECTION OF MYCOBACTERIA<br/>[FR] DÉTECTION DE MYCOBACTÉRIES
  申请人：ISIS INNOVATION

  公开号：WO2011030160A1

  公开（公告）日：2011-03-17

  A method for determining the presence of mycobacteria species in an organism or biological sample, the method comprising adding to the organism or biological sample a probe molecule comprising a substrate and a label, which probe molecule can be incorporated into mycobacteria, the presence of mycobacteria being determined by a detector responsive to the presence of the label, optionally after applying a stimulus; suitable probe molecules include compounds comprising a label and a substrate, which label is can be detected by a detector responsive to the presence of the label, optionally after applying a stimulus, characterised by compound being able to engage with the active site of Antigen 85B (Ag85B) such that it can form simultaneous hydrogen bonds with two or more amino acids in the active site selected from Arg 43, Trp 264, Ser126, His 262 and Leu 42, or the corresponding amino acids in Antigen 85A (Ag85A) or Antigen 85C (Ag85C), at least one of which is with Ser126.

  一种用于确定生物体或生物样本中结核分枝杆菌种类存在的方法，该方法包括向生物体或生物样本中添加一种探针分子，该探针分子包括底物和标记，该探针分子可以被结核分枝杆菌所吸收，通过对标记的存在做出反应的探测器确定结核分枝杆菌的存在，可选地，在施加刺激后进行；适用的探针分子包括包含标记和底物的化合物，该标记可以被对标记的存在做出反应的探测器检测到，可选地，在施加刺激后进行，其特征在于该化合物能够与抗原85B（Ag85B）的活性位点结合，从而能够与所选活性位点中的两个或更多氨基酸同时形成氢键，所选活性位点包括Arg 43、Trp 264、Ser126、His 262和Leu 42，或者抗原85A（Ag85A）或抗原85C（Ag85C）中对应的氨基酸，其中至少一个与Ser126形成氢键。
• Synthesis, trehalase hydrolytic resistance and inhibition properties of 4- and 6-substituted trehalose derivatives
  作者：Shari Dhaene、Johan Van der Eycken、Koen Beerens、Jorick Franceus、Tom Desmet、Jurgen Caroen

  DOI：10.1080/14756366.2020.1837125

  日期：2020.1.1

  activity could be of interest. In this study, 34 4- and 6-O-substituted trehalose derivatives were synthesised using an ether- or carbamate-type linkage. Their hydrolysis susceptibility and inhibitory properties were determined against two trehalases, i.e. porcine kidney and Mycobacterium smegmatis. With the exception of three weakly hydrolysable 6-O-alkyl derivatives, the compounds generally showed to be

  摘要 尽管海藻糖由于其药物潜力最近已引起人们的兴趣，但由于其生物利用度低而阻碍了其临床应用。因此，保持生物活性的耐水解的海藻糖类似物可能是令人感兴趣的。在这项研究中，使用醚或氨基甲酸酯型键合成了34种4-和6- O取代的海藻糖衍生物。测定了它们对两种海藻糖酶的水解敏感性和抑制特性，即猪肾和耻垢分枝杆菌。除了三个弱水解的6- O-烷基衍生物，该化合物通常显示出完全抗性。此外，许多衍生物被证明是这些海藻糖酶之一或两者的抑制剂。对于猪肾海藻糖酶的最强抑制剂，可以测定约50 mM的IC 50值，而几种化合物显示出针对耻垢分枝杆菌海藻糖酶的亚mM IC 50值。进行了对接研究以解释观察到的取代模式对猪肾海藻糖酶抑制活性的影响。
• α-D-Glucosylation by 6-<i>O</i>-Acetyl-2,3,4-tri-<i>O</i>-benzyl-D-glucopyranose Using Trimethylsilyl Triflate and Pyridine. Synthesis of α-Maltosyl and α-Isomaltosyl α-D-Glucosides
  作者：Shinkiti Koto、Kazuo Yago、Shonosuke Zen、Fumiya Tomonaga、Shigehiko Shimada

  DOI：10.1246/bcsj.59.411

  日期：1986.2

  system in dichloromethane proceeded with good α-selectivity irrespective of the type of the hydroxyl group. This α-D-glucosylation was applied for the synthesis of O-α-D-glucopyranosyl-(1→4)- and -(1→6)-α-D-glucopyranosyl α-D-glucopyranosides from α,α-trehalose.

  甲基 2,3,4-三-O-苄基-α-D-吡喃葡萄糖苷和甲基 2,3,6-三-O-苄基-β-D-吡喃葡萄糖苷通过 2,3,4,6 的 D-葡萄糖基化-四-O-苄基-α-D-吡喃葡萄糖使用吡啶和过量的三甲基甲硅烷基三氟甲磺酸酯在二氯甲烷、1,2-二甲氧基乙烷和乙腈中进行。在给定的溶剂中，反应的选择性取决于葡萄糖基受体的羟基类型。这些受体与 6-O-乙酰基-2,3,4-三-O-苄基-D-吡喃葡萄糖在二氯甲烷中使用该试剂系统进行 D-葡糖基化，无论羟基的类型如何，都具有良好的 α-选择性。这种 α-D-葡萄糖基化用于从 α,α-海藻糖合成 O-α-D-吡喃葡萄糖苷-(1→4)- 和 -(1→6)-α-D-吡喃葡萄糖苷 α-D-吡喃葡萄糖苷.
• Synthesis of trehalose-based compounds and their inhibitory activities against Mycobacterium smegmatis
  作者：Jinhua Wang、Bryan Elchert、Yu Hui、Jon Y. Takemoto、Mekki Bensaci、John Wennergren、Huiwen Chang、Ravi Rai、Cheng-Wei Tom Chang

  DOI：10.1016/j.bmc.2004.09.033

  日期：2004.12

  The synthesis of a library of trehalose-based compounds has been accomplished, and their activities against mycobacterium smegmatis have been determined. A preliminary structure-activity relationship (SAR) is reported. Despite not having a potent lead, one of the trehalose derivatives displays strong activity when applied with isoniazid (INH), which is known to have low sterilizing activity. The bacteriocidal nature of our compounds against Mycobacterium may be significant for the development of new therapies against tuberculosis. (C) 2004 Elsevier Ltd. All rights reserved.
• Rational design of first generation inhibitors for trehalose 6-phosphate phosphatases
  作者：Chunliang Liu、Debra Dunaway-Mariano、Patrick S. Mariano

  DOI：10.1016/j.tet.2017.01.041

  日期：2017.3

  In this study, trehalose 6-phosphate phosphatase (T6PP) was targeted for inhibitor development. T6PP catalyzes the hydrolysis of trehalose-6-phosphate to form trehalose and inorganic phosphate, a reaction essential to important fungal, bacterial, and nematodal pathogens. At the current time, there are no specific inhibitors of T6PP available to serve as tools for interrogating its structure and function nor as leads for pharmaceutical applications. Herein, we describe the synthesis of non-hydrolysable mimics of trehalose-6-phosphate, which incorporate 6-sulfate (1),-phosphonate (2),-fluorophosphonate (3) and boronate (4) groups in place of the 6-phosphate moiety of the substrate. The inhibitory efficacies of these adducts were evaluated against trehalose 6-phosphatephosphatases selected from evolutionarily distant pathogenic bacteria and nematodes. Phosphonates 2 and 3 were found to display good inhibitory activities against the T6PPs, while the sulfate analog, trehalose-6-sulfate, proved to be a particularly effective broad-spectrum inhibitor of these phosphatases and an ideal prototype for optimization. (C) 2017 Elsevier Ltd. All rights reserved.