6-氨基-6-脱氧-alpha-D-吡喃葡萄糖基6-氨基-6-脱氧-alpha-D-吡喃葡萄糖苷 | 30923-00-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 6-氨基-6-脱氧-alpha-D-吡喃葡萄糖基6-氨基-6-脱氧-alpha-D-吡喃葡萄糖苷
• 英文名称: 6,6'-diamino-6,6'-dideoxy-α,α-D-trehalose
• 英文别名: 6,6'-diamino-6,6'-dideoxy-α,α'-trehalose；6,6'-diamino-6,6'-dideoxy-α,α-trehalose；6,6'-diamino-6,6'-deoxy-α,α'-trehalose；(2R,3S,4S,5R,6R)-2-(aminomethyl)-6-[(2R,3R,4S,5S,6R)-6-(aminomethyl)-3,4,5-trihydroxy-tetrahydropyran-2-yl]oxy-tetrahydropyran-3,4,5-triol；(2R,3S,4S,5R,6R)-2-(aminomethyl)-6-[(2R,3R,4S,5S,6R)-6-(aminomethyl)-3,4,5-trihydroxyoxan-2-yl]oxyoxane-3,4,5-triol
• CAS: 30923-00-3
• 化学式: C₁₂H₂₄N₂O₉
• 分子量: 340.331
• InChiKey: PRCXQNVVPVYNAA-LIZSDCNHSA-N

物化性质

• 沸点：
  636.8±55.0 °C(Predicted)
• 密度：
  1.65±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  201
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  6-氨基-6-脱氧-alpha-D-吡喃葡萄糖基6-氨基-6-脱氧-alpha-D-吡喃葡萄糖苷 在 palladium on activated charcoal ammonium hydroxide 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 64.0h， 生成
  参考文献：
  名称：

  α,α-Trehalose derivatives bearing guanidino groups as inhibitors to HIV-1 Tat–TAR RNA interaction in human cells

  摘要：

  Replication of HIV-1 requires specific interactions of Tat protein with TAR RNA. Disruption of Tat TAR RNA interaction could inhibit HIV-1 replication. Here four target compounds were designed and synthesized to bind to TAR RNA for blocking the interaction of Tat-TAR RNA. The core molecule 6,6'-diamino-6,6'-dideoxy-alpha,alpha-trehalose was obtained from selective bromination of, alpha,alpha-trehalose at C-6,6', followed by acetylation, azide displacement, deacetylation, and reduction. Coupling of the core molecule with the protected amino acid, then deprotection and guanidinylation generated the novel alpha,alpha-trehalose derivatives. Their abilities to inhibit Tat-TAR RNA interaction in human cells were determined by a Tat-dependent HIV-1 LTR-driven CAT assays. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.073
• 作为产物：
  描述：

  海藻糖 生成 6-氨基-6-脱氧-alpha-D-吡喃葡萄糖基6-氨基-6-脱氧-alpha-D-吡喃葡萄糖苷
  参考文献：
  名称：

  Synthesis, conformational flexibility and preliminary complexation behaviour of α,α′-trehalose-based macrocycles containing thiourea spacers

  摘要：

  报告了一种高效合成大环配体的方法，该配体包含两个δ,δâ²-三卤糖亚基，通过 1,3-thiourea 间隔物在主 C-6,6â²位置连接；NâC(S) 键的 Z/E 构型受分子内氢键和立体因素的影响。

  DOI：

  10.1039/c39950000057
• 作为试剂：
  描述：

  海藻糖 在 吡啶 、 6-氨基-6-脱氧-alpha-D-吡喃葡萄糖基6-氨基-6-脱氧-alpha-D-吡喃葡萄糖苷 、 calcium carbonate 作用下， 以 水 、 丙酮 为溶剂， 生成 6,6'-diamino-6,6'-dideoxy-α,α'-trehalose 6,4:6',4'-bis(cyclic thiocarbamate)
  参考文献：
  名称：

  Synthesis, conformational flexibility and preliminary complexation behaviour of α,α′-trehalose-based macrocycles containing thiourea spacers

  摘要：

  报告了一种高效合成大环配体的方法，该配体包含两个δ,δâ²-三卤糖亚基，通过 1,3-thiourea 间隔物在主 C-6,6â²位置连接；NâC(S) 键的 Z/E 构型受分子内氢键和立体因素的影响。

  DOI：

  10.1039/c39950000057

文献信息

• Mono- and dialdehyde of trehalose: new synthons to prepare trehalose bio-conjugates
  作者：Valentina Greco、Sebastiano Sciuto、Enrico Rizzarelli

  DOI：10.1039/d1ob01816g

  日期：——

  disaccharide and also some of its derivatives have been shown to have a number of interesting properties that indicate their importance in the treatment of certain human diseases. Differentiating the two glucosyl moieties in the trehalose molecule has often been a synthetic challenge. We report here an easy way to obtain the monoaldehyde of trehalose, as well as the relevant symmetrical dialdehyde. The reactivity

  海藻糖是葡萄糖的非还原性二糖，是一种天然的生物活性无毒糖。它存在于许多生物体中，当它们的细胞暴露于压力条件时会合成它。虽然不是由哺乳动物细胞产生，但这种二糖及其一些衍生物已被证明具有许多有趣的特性，表明它们在治疗某些人类疾病中的重要性。区分海藻糖分子中的两个葡糖基部分通常是一项合成挑战。我们在这里报告了一种简单的方法来获得海藻糖的单醛，以及相关的对称二醛。这些合成子的分子结构中涉及的醛官能团的反应性允许容易地制备相应的海藻糖氨基或羧基衍生物，
• Supramolecular structures of substituted α,α′-trehalose derivatives
  作者：Thomas C. Baddeley、Iain G. Davidson、Christopher Glidewell、John N. Low、Janet M. S. Skakle、James L. Wardell

  DOI：10.1107/s0108768104010912

  日期：2004.8.1

  The structures of five substituted α,α′-trehalose trehalose derivatives have been determined, and these are compared with those of four previously published analogues. In 2,2′,3,3′,4,4′-hexaacetato-6,6′-bis-O-methylsulfonyl-α,α′-trehalose, C₂₆H₃₈O₂₁S₂, where the molecules lie across twofold rotation axes in the space group C2, a single C—H...O=S hydrogen bond links the molecules into sheets. 2,2′,3,3′,4,4′-Hexaacetato-6,6′-bis-O-(4-toluenesulfonyl)-α,α′-trehalose, C₃₈H₄₆O₂₁S₂, crystallizes with Z′ = 2 in the space group P2₁2₁2₁ and a combination of three C—H...O hydrogen bonds, each having a carbonyl O atom as an acceptor, and a C—H...π(arene) hydrogen bond link the molecules into a three-dimensional framework. 2,2′,3,3′,4,4′-Hexaacetato-6,6′-diazido-α,α′-trehalose, C₂₄H₃₂N₆O₁₅, crystallizes as a partial ethanol solvate and three C—H...O hydrogen bonds link the substituted trehalose molecules into a three-dimensional framework. In 2,2′,3,3′-tetraacetato-6,6′-bis(N-acetylamino)-α,α′-trehalose dihydrate, C₂₄H₃₆N₂O₁₅·2H₂O, the substituted trehalose molecules lie across twofold rotation axes in the space group P2₁2₁2 and a three-dimensional framework is generated by the combination of O—H...O and N—H...O hydrogen bonds. The diaminotrehalose molecules in 6,6′-diamino-α,α′-trehalose dihydrate, C₁₂H₂₄N₂O₉.2(H₂O), lie across twofold rotation axes in the space group P4₃2₁2: a single O—H...N hydrogen bond links the trehalose molecules into sheets, which are linked into a three-dimensional framework by O—H...O hydrogen bonds.

  我们确定了五种取代的 α,α′-三卤糖三卤糖衍生物的结构，并将其与之前发表的四种类似物的结构进行了比较。在 2,2′,3,3′,4,4′-六乙酰氧基-6,6′-双-O-甲基磺酰基-α,α′-三卤糖 C26H38O21S2 中，分子位于空间群 C2 的两倍旋转轴上，一个 C-H...O=S 氢键将分子连接成片状。2,2′,3,3′,4,4′-六乙酰-6,6′-双-O-（4-甲苯磺酰）-α,α′-三卤糖，C38H46O21S2，在空间群 P212121 中以 Z′ = 2 结晶，由三个 C-H...O.氢键组合而成。...O氢键（每个氢键都有一个羰基O原子作为受体）和一个C-H...π（芴）氢键将分子连接成一个三维框架。2,2′,3,3′,4,4′-六乙酰-6,6′-叠氮-α,α′-三卤糖 C24H32N6O15 结晶为部分乙醇溶解物，三个 C-H...O 氢键将取代的三卤糖分子连接成一个三维框架。在 2,2′,3,3′-四乙酰-6,6′-双（N-乙酰氨基）-α,α′-曲哈洛糖二水合物 C24H36N2O15-2H2O 中，取代的曲哈洛糖分子位于空间群 P21212 的两倍旋转轴上，通过 O-H...O 和 N-H...O 氢键的结合形成了一个三维框架。6,6′-diamino-α,α′-trehalose dihydrate（C12H24N2O9.2(H2O)）中的二氨基海藻糖分子横跨空间群 P43212 中的两个旋转轴：一个 O-H...N 氢键将海藻糖分子连接成片状，这些片状分子通过 O-H...O 氢键连接成一个三维框架。
• Gemini Surfactants with a Disaccharide Spacer
  作者：Fredric M. Menger、Bessie N. A. Mbadugha

  DOI：10.1021/ja0033178

  日期：2001.2.1

  behavior of Series-A geminis in many ways parallels that of phospholipids and simple double-chain surfactants. It is as if the trehalose is less of a spacer than a large but conventional headgroup. In contrast, cationic Series-B geminis are water soluble and form micelles with critical micelle concentrations an order of magnitude lower than that of corresponding conventional surfactants. Molecular modeling

  双子表面活性剂是具有（按顺序）以下的两亲物：烃尾/极性基团/间隔基/极性基团/烃尾。最近，工业和学术实验室都对双子座产生了广泛的兴趣。在目前的贡献中，已经合成了两个相关的双子星家族，它们都使用海藻糖（一种二糖）作为极性间隔物。一个系列，A 系列，是非离子型的，并具有将长链与海藻糖间隔基分开的酰胺基团。另一个家族，B 系列，具有将长链连接到海藻糖间隔物的季铵离子。发现尽管有两个酰胺和多个羟基，A 系列双子座还是不溶于水的。当水合或挤压时，这些双子座在其转变温度（通过量热法确定）之上形成微观可见的囊泡和管状结构。由这些 Geminis 构建的不溶性单分子膜具有由糖间隔基主导的界面区域，尽管分子间链/链相互作用似乎稳定了膜。因此，A 系列双子座的行为在许多方面与磷脂和简单双链表面活性剂的行为相似。就好像海藻糖比大而传统的头部基团更像是一个间隔区。相比之下，阳离子 B 系列双子是水溶性的，并形成临
• Synthesis, Structure, and Inclusion Capabilities of Trehalose-Based Cyclodextrin Analogues (Cyclotrehalans)
  作者：David Rodríguez-Lucena、Juan M. Benito、Eleuterio Álvarez、Carlos Jaime、Javier Perez-Miron、Carmen Ortiz Mellet、José M. García Fernández

  DOI：10.1021/jo800048s

  日期：2008.4.1

  Concise and efficient strategies toward the synthesis of D-2h- and D-3h-symmetric cyclodextrin analogues alternating alpha,alpha'-trehalose disaccharide subunits and pseudoamide segments (cyclotrehalans, CTs) are reported. The conformational properties of these cyclooligosaccharides are governed by the rigidity of the alpha,alpha'-trehalose disaccharide repeating unit and the partial double-bond character of the N-(C=X) linkages. In contrast to the typical concave-shaped cavity of cyclodextrins (CDs), CTs feature a convex-shaped hydrophobic cavity in which the beta-face of the monosaccharide subunits is oriented toward the inner side, as supported by NMR and modeling (molecular mechanics and dynamics) studies. In the case of cyclodimeric CTs (CT2s), the existence of intramolecular hydrogen bonds results in collapsed cavities, too small to allow the formation of inclusion complexes with organic molecules. Cyclotrimeric CTs (CT3s) display cavity sizes that are intermediate between those of alpha CD and beta CD, ideally suited for the complexation of complementary guests with ternary symmetry such as adamantane 1-carboxylate (AC). The higher flexibility of the pseudoamide bridges as compared with classical glycosidic linkages endow these glyconanocavities with some conformational adaptability properties, making them better suited than CDs for complexation of angular guests, as seen from comparative inclusion capability experiments against the fluorescent probes 6-p-toluidinonaphthalene-2-sulfonate (TNS; linear) and 8-anilinonaphthalene-1-sulfonate (ANS; angular).
• Synthesis and biological evaluation of trehalose analogs as potential inhibitors of mycobacterial cell wall biosynthesis
  作者：Jerry D. Rose、Joseph A. Maddry、Robert N. Comber、William J. Suling、Larry N. Wilson、Robert C. Reynolds

  DOI：10.1016/s0008-6215(01)00288-9

  日期：2002.2

  Analogs of trehalose are reported that were designed to interfere with mycolylation pathways in the mycobacterial cell wall. Several derivatives of 6,6'-dideoxytrehalose, including N,N'-dialkylamino and 6,6'-bis(sulfonamido) analogs, were prepared and evaluated for antimycobacterial activity against Mycobacterium tuberculosis H(37)Ra and a panel of clinical isolates of Mycobacterium avium, 6,6'-Diamitiotrehalose and its diazido precursor were both inactive, but significant activity apparently related to aliphatic chain length was found among the sulfonamides, N-alkylamines, and one of the amidines. (C) 2002 Elsevier Science Ltd. All rights reserved.