4,6;4',6'-di-O-benzylidene-α,α-D-trehalose | 18929-82-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,6;4',6'-di-O-benzylidene-α,α-D-trehalose
• 英文别名: 4,6:4',6'-di-O-benzylidene-α,α-trehalose；4,6:4',6'-di-O-benzylidene-α-D-trehalose；4,6:4',6'-di-O-benzylidene trehalose；(2R,4aR,6R,7R,8R,8aS)-6-[[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol
• CAS: 18929-82-3；60949-45-3；97390-02-8；127128-52-3
• 化学式: C₂₆H₃₀O₁₁
• 分子量: 518.518
• InChiKey: ZVSNVLCFTYGYQP-ZFSXDRMKSA-N

物化性质

• 熔点：
  140-145 °C(Solv: toluene (108-88-3); water (7732-18-5))
• 沸点：
  772.2±60.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  37
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  146
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  4,6;4',6'-di-O-benzylidene-α,α-D-trehalose 在 甲醇 、 对甲苯磺酸 作用下， 反应 0.03h， 以98%的产率得到海藻糖
  参考文献：
  名称：

  Sonochemistry:  A Powerful Way of Enhancing the Efficiency of Carbohydrate Synthesis

  摘要：

  [GRAPHICS]Using sonication as a means of facilitating organic reactions in carbohydrate chemistry was explored under the conditions used for traditional organic synthesis. An array of representative reactions, including hydroxy group manipulation ( acylation, protection/deprotection, acyl group migration), thioglycoside synthesis, azidoglycoside synthesis, 1,3-dipolar cycloaddition and reductive cleavage of benzylidene, commonly used in the synthesis of carbohydrate derivatives was examined. A series of glycosylation reactions that employ thioglycosides, glycosyl trichloroacetimidate, glycosyl bromide and glycosyl acetate as the glycosyl donors was also examined. Our results demonstrate that sonication can significantly shorten the reaction time, enhance the reactivity of reactant and lead to superior yield and excellent stereoselectivity. More importantly, a general protocol of glycosylation may finally be developed. Sonication is compatible to the conditions used for traditional organic synthesis. We believe that sonication can also be applied to other areas of synthetic processes.

  DOI：

  10.1021/jo060374w
• 作为产物：
  描述：

  海藻糖 、 苯甲醛二甲缩醛 在 对甲苯磺酸 作用下， 以90%的产率得到4,6;4',6'-di-O-benzylidene-α,α-D-trehalose
  参考文献：
  名称：

  用于膜蛋白研究的十二烷基海藻糖苷去污剂的合成和性质

  摘要：

  糖基洗涤剂，主要来自麦芽糖或葡萄糖，在膜蛋白的提取、增溶、稳定和结晶中占主导地位。受海藻糖广泛用于保护生物大分子和脂质双层结构的启发，我们合成了新的海藻糖苷去污剂，用于膜蛋白研究的潜在应用。我们设计了四种十二烷基海藻糖苷的有效合成方法，每种十二烷基海藻糖苷的 12 碳烷基链连接到海藻糖的不同羟基，从而呈现结构多样但相关的洗涤剂家族。评估洗涤剂的物理特性，包括溶解度、疏水性、临界胶束浓度 (CMC) 和胶束大小，并与最流行的麦芽糖苷类似物 β- d 进行比较。-十二烷基麦芽糖苷 (DDM)，由于不同的分子几何形状和所得胶束中可能的极性基团相互作用而彼此不同。还在甲醇中获得了 2-十二烷基海藻糖苷 (2-DDTre) 的晶体，晶体堆积显示相邻海藻糖基团之间存在多个 H 键相互作用。测试了少数海藻糖苷去污剂对伤害感受素/孤啡肽 FQ 肽受体 (ORL1) 和 MsbA 的溶解和稳定作用，它们分别属于

  DOI：

  10.1021/la3020404

文献信息

• Synthesis of Per- and Poly-Substituted Trehalose Derivatives: Studies of Properties Relevant to Their Use as Excipients for Controlled Drug Release
  作者：Thomas C. Baddeley、James L. Wardell

  DOI：10.1080/07328300902887672

  日期：2009.5.22

  substituents, included 6,6′-N,N′ -diamido-6,6′ -dideoxy-α,α -trehalose derivatives, 6,6′ -bis(1,2,3,4-tetra-O-acetyl-β -D-glucopyranuronyl)-α, α -trehalose derivatives, 2,2′,3,3′ -tetra-O-acetyl-6,6′ -bis-(1,2,3,4-tetra-O-acetyl-β-D-glucopyranuronyl)-4,4′ -di-O-acyl-α,α-trehalose, 2, 2′, 3, 3′ -tetra-O-acetyl-6-(1,2,3,4-tetra-O-acetyl-β-D-glucopyranuronyl)-4,4′,6′ -tri-O-acyl-α,α-trehalose, and 2,2′,3,3′,4

  已经制备了具有海藻糖核心的全取代和多取代的寡糖衍生物，并评估了它们在控释制剂中用作赋形剂的潜力。通常具有酰基和酰胺基取代基的合成化合物包括6,6'- N，N'-二叠氮基-6,6'-二脱氧-α，α-海藻糖衍生物，6,6'-双（1,2,3） ，4-四-O-乙酰基-β-D-吡喃葡萄糖醛酸基）-α，α-海藻糖衍生物，2,2'，3,3'-四-O-乙酰基-6,6'-双-（1,2 ，3,4-四-O-乙酰基-β-D-吡喃葡萄糖醛酸）-4,4'-二-O-酰基-α，α-海藻糖，2，2'，3，3'-四-O-乙酰基-6-（1,2,3,4-四-O乙酰基β-d-glucopyranuronyl）-4,4'，6' -三ö酰基-α，α -海藻糖，和2,2'，3,3'，4,4'-hexa- ö -乙酰基-6,6'-双-（1,2,3,4-四-O-乙酰基-6- O-琥珀酰基-β-D-吡喃葡萄糖醛酸基）-α，α-海藻糖。用NMR
• Click Multivalent Heterogeneous Neoglycoconjugates - Modular Synthesis and Evaluation of Their Binding Affinities
  作者：Mariano Ortega-Muñoz、Francisco Perez-Balderas、Julia Morales-Sanfrutos、Fernando Hernandez-Mateo、Joaquín Isac-García、Francisco Santoyo-Gonzalez

  DOI：10.1002/ejoc.200801169

  日期：2009.5

  The efficient synthesis of structurally diverse, multivalent, heterogeneous neoglycoconjugates by means of a series of different click-based strategies is described. The methodology is highly efficient and versatile allowing for easy access to a series of mannose (α-Man)-containing glycoconjugates differing in their valency, nature of the scaffold, nature of the constitutive sugars and length of the

  描述了通过一系列不同的基于点击的策略有效合成结构多样、多价、异质的新糖缀合物。该方法高效且通用，允许轻松获取一系列含甘露糖 (α-Man) 的糖缀合物，这些糖缀合物的价数、支架的性质、组成性糖的性质和接头的长度都不同。评估了这些结构参数对这些糖模拟物对刀豆球蛋白 A (Con A) 的结合亲和力的影响。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• 새로운 트레할로스 중심을 갖는 양친매성 화합물 및 이의 활용
  申请人：Industry-University Cooperation Foundation Hanyang University ERICA Campus 한양대학교 에리카산학협력단(120120008551) Corp. No ▼ 131471-0017977BRN ▼134-82-10205

  公开号：KR20200068883A

  公开（公告）日：2020-06-16

  본 발명은 새롭게 개발한 트레할로스 기반의 양친매성 화합물, 이의 제조방법 및 이를 이용하여 막단백질을 추출, 용해화, 안정화, 결정화 또는 분석하는 방법에 관한 것이다. 또한, 이 화합물은 기존의 화합물보다 다양한 구조와 특성을 지닌 막단백질들을 세포막에서 효율적으로 추출하고 이를 수용액에서 장기간 안정적으로 보관할 수 있고, 이를 통해 그 기능분석 및 구조 분석에 활용될 수 있다. 막단백질 구조 및 기능 분석은 신약 개발에 밀접한 관계가 있는 만큼 현 생물학 및 화학에서 가장 관심을 갖고 있는 분야 중 하나이다.

  This invention relates to a newly developed trehalose-based amphiphilic compound, its manufacturing method, and a method for extracting, solubilizing, stabilizing, crystallizing, or analyzing membrane proteins using it. Furthermore, this compound efficiently extracts membrane proteins with diverse structures and characteristics from cell membranes compared to conventional compounds, allowing for long-term stable storage in solution, thereby enabling their functional and structural analysis. The analysis of membrane protein structure and function is closely related to drug development and is therefore one of the most intriguing areas of interest in modern biology and chemistry.
• Trehalose-cored amphiphiles for membrane protein stabilization: importance of the detergent micelle size in GPCR stability
  作者：Manabendra Das、Yang Du、Jonas S. Mortensen、Manuel Ramos、Lubna Ghani、Ho Jin Lee、Hyoung Eun Bae、Bernadette Byrne、Lan Guan、Claus J. Loland、Brian K. Kobilka、Pil Seok Chae

  DOI：10.1039/c8ob03153c

  日期：——

  and/or crystallization with currently available detergents and thus there are major efforts to develop novel detergents with enhanced properties. Here, a novel class of trehalose-cored amphiphiles are introduced, with multiple alkyl chains and carbohydrates projecting from the trehalose core unit are introduced. A few members displayed enhanced protein stabilization behavior compared to the benchmark

  尽管它们在生物学和药物化学中很重要，但膜蛋白的结构和功能研究仍存在重大挑战。为了研究各种膜蛋白，至关重要的是拥有正确的去污剂，以有效地从天然膜中提取和稳定蛋白，以进行生物化学/生物物理下游分析。但是许多膜蛋白，特别是真核膜蛋白，用目前可用的去污剂难以稳定和/或结晶，因此，人们致力于开发具有增强性能的新型去污剂。在此，介绍了一类新型的以海藻糖为核心的两亲物，并引入了多个烷基链，并介绍了从海藻糖核心单元伸出的碳水化合物。Ñ十二烷基-β- d -maltoside（DDM），对于多个测试膜蛋白：（ⅰ）一个细菌亮氨酸转运体（LeuT），（ii）所述R.荚膜光合superassembly，以及（iii）人类β 2肾上腺素能受体（β 2 AR）。由于合成的便利性和它们对一系列膜蛋白的良好行为，这些试剂在膜蛋白研究中具有潜力。另外，这里讨论的洗涤剂性能与功效关系将指导新型洗涤剂的未来设计。
• 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。