6,6'-dideoxy-6,6'-diiodo-α,α'-trehalose | 52290-50-3

• 物质功能分类: 生物化工 - 生化试剂
• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6,6'-dideoxy-6,6'-diiodo-α,α'-trehalose
• 英文别名: 6,6'-diiodo-6,6'-dideoxy-α,α'-trehalose；(2S,3S,4S,5R,6R)-2-(iodomethyl)-6-[(2R,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(iodomethyl)oxan-2-yl]oxyoxane-3,4,5-triol
• CAS: 52290-50-3
• 化学式: C₁₂H₂₀I₂O₉
• 分子量: 562.094
• InChiKey: HNRYAZDODAETJR-LIZSDCNHSA-N

物化性质

• 沸点：
  688.5±55.0 °C(Predicted)
• 密度：
  2.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 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：
  149
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  6,6'-dideoxy-6,6'-diiodo-α,α'-trehalose 在 苄胺 、 盐酸 、 氢气 、 palladium(II) hydroxide 作用下， 以 水 为溶剂， 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：

  PROCESS FOR THE PRODUCTION OF DATH AND INTERMEDIATES THEREOF

  摘要：

  The present technology is direct to methods of producing 6,6′-diamino-6,6′-deoxy-trehalose (“DATH”) or a salt thereof. The methods include optionally protecting one or more hydroxyl groups of D-trehalose and converting the primary hydroxyl groups of D-trehalose to product DATH or a salt thereof through use of a halogen, azide, and/or protected amine to. The present technology is also direct to intermediate products of the methods.

  公开号：

  US20220389044A1
• 作为产物：
  描述：

  海藻糖 在 碘 、 三苯基膦 、 sodium methylate 作用下， 以 N,N-二甲基甲酰胺 、 甲醇 为溶剂， 反应 4.5h， 生成 6,6'-dideoxy-6,6'-diiodo-α,α'-trehalose
  参考文献：
  名称：

  两种β-环糊精通过海藻糖部分作为接头的合成组装1

  摘要：

  合成的组件2β环糊精（CDS），使用6,6'-二iodotrehalose衍生物作为一个独特的接头由在用于Birch还原和随后的S液位氨一锅反应的方式被有效地完成Ñ 2更换。由于CD的空腔和海藻糖接头的相似结构的一部分，独特的硫化物连接的CD二聚体显示出更宽的疏水区域。使用 TNS（2-对甲苯胺基萘-6-磺酸盐）作为模型客体化合物，初步检查了 CD 二聚体的包含特性。

  DOI：

  10.1016/j.tetlet.2021.153287

文献信息

• [EN] BRARTEMICIN ANALOGUES<br/>[FR] ANALOGUES DE BRARTÉMICINE
  申请人：VICTORIA LINK LTD

  公开号：WO2019088854A1

  公开（公告）日：2019-05-09

  The invention relates to brartemicin analogues of Formula (IV) and their uses. These compounds are potent Mincle agonists and Th1-stimulating vaccine adjuvants.

  这项发明涉及公式（IV）的brartemicin类似物及其用途。这些化合物是强效的Mincle激动剂和Th1刺激疫苗佐剂。
• Isothiocyanates and cyclic thiocarbamates of α, α′-trehalose, sucrose, and cyclomaltooligosaccharides
  作者：JoséManuel García Fernández、Carmen Ortiz Mellet、JoséLuis Jiménez Blanco、José Fuentes Mota、Andrée Gadelle、Annie Coste-Sarguet、Jacques Defaye

  DOI：10.1016/0008-6215(94)00312-4

  日期：1995.3

  amino sugars with thiophosgene. In the absence of base, all isothiocyanates were stable and could be stored and acetylated without decomposition. In the presence of triethylamine, 6,6'-dideoxy-6,6'-diisothiocyanato-alpha,alpha'-trehalose underwent intramolecular cyclisation involving HO-4 to give the corresponding bis(cyclic thiocarbamate). The product of cyclisation at a single glucopyranosyl unit

  6,6'-Dideoxy-6,6'-diisothiocyanato-alpha，alpha'-海藻糖（4），6-deoxy-6-isothiocyanato-alpha-D-果糖呋喃糖β-D-果糖吡喃糖1,2'：2 ，1'-二酐（11），6,6'-二脱氧-6,6'-二异硫氰酸根合蔗糖（16）和全（6-脱氧-6-异硫氰酸根合）-环麦芽六糖（23），-环麦芽庚糖（27）和通过使相应的氨基糖与硫光气反应以高收率制备β-环麦芽八糖（31）。在没有碱的情况下，所有异硫氰酸酯都是稳定的，可以储存和乙酰化而不会分解。在三乙胺的存在下，将涉及HO-4的6,6'-二脱氧-6,6'-二异硫氰基-α，α'-海藻糖进行分子内环化反应，得到相应的双（环状硫代氨基甲酸酯）。在上述二异硫氰酸酯与混合的（H +，HO-）离子交换树脂的处理中，获得了在单个吡喃葡萄糖基单元上的环化产物。在相同的反应条件下，6,6'-二脱氧-6
• Poly(trehalose): Sugar-Coated Nanocomplexes Promote Stabilization and Effective Polyplex-Mediated siRNA Delivery
  作者：Antons Sizovs、Lian Xue、Zachary P. Tolstyka、Nilesh P. Ingle、Yaoying Wu、Mallory Cortez、Theresa M. Reineke

  DOI：10.1021/ja404941p

  日期：2013.10.16

  When nanoparticles interact with their environment, the nature of that interaction is governed largely by the properties of its outermost surface layer. Here, we exploit the exceptional properties of a common disaccharide, trehalose, which is well-known for its unique biological stabilization effects. To this end, we have developed a synthetic procedure that readily affords a polymer of this disaccharide, poly-(methacrylamidotrehalose) or "poly(trehalose)" and diblock copolycations containing this polymer with 51 repeat units chain extended with aminoethylmethacrylamide (AEMA) at three degrees of polymerization (n = 34, 65, and 84). Two series of experiments were conducted to study these diblock copolymers in detail and to compare their properties to two control polymers [PEG-P(AEMA) and P(AEMA)]. First, we demonstrate that the poly(trehalose) coating ensures colloidal stability of polyplexes containing siRNA in the presence of high salt concentrations and serum proteins. Poly(trehalose) retains the ability of trehalose to lower the phase transition energy associated with water freezing and can protect siRNA polyplexes during freeze-drying, allowing complete nanoparticle resuspension without loss of biological function. Second, we show that siRNA polyplexes coated with poly(trehalose) have exceptional cellular internalization into glioblastoma cells that proceeds with zero-order kinetics. Moreover, the amount of siRNA delivered by poly(trehalose) block copolycations can be controlled by the siRNA concentration in cell culture media. Using confocal microscopy we show that trehalose-coated polyplexes undergo active trafficking in cytoplasm upon internalization and significant siRNA-induced target gene down-regulation was achieved with an IC50 of 19 nM. These findings coupled with a negligible cytotoxicity suggests that poly(trehalose) has the potential to serve as an important component of therapeutic nanoparticle formulations of nucleic acids and has great promise to be extended as a new coating for other nanobased technologies and macromolecules, in particular, those related to nanomedicine applications.
• Trehalose- and Glucose-Derived Glycoamphiphiles: Small-Molecule and Nanoparticle Toll-Like Receptor 4 (TLR4) Modulators
  作者：Julio Rodriguez Lavado、Stefania E. Sestito、Roberto Cighetti、Eva M. Aguilar Moncayo、Alja Oblak、Duško Lainšček、José Luis Jiménez Blanco、José Manuel García Fernández、Carmen Ortiz Mellet、Roman Jerala、Valentina Calabrese、Francesco Peri

  DOI：10.1021/jm501182w

  日期：2014.11.13

  An increasing number of pathologies have been linked to Toll-like receptor 4 (TLR4) activation and signaling, therefore new hit and lead compounds targeting this receptor activation process are urgently needed. We report on the synthesis and biological properties of glycolipids based on glucose and trehalose scaffolds which potently inhibit TLR4 activation and signaling in vitro and in vivo. Structure-activity relationship studies on these compounds indicate that the presence of fatty ester chains in the molecule is a primary prerequisite for biological activity and point to facial amphiphilicity as a preferred architecture for TLR4 antagonism. The cationic glycolipids here presented can be considered as new lead compounds for the development of drugs targeting TLR4 activation and signaling in infectious, inflammatory, and autoimmune diseases. Interestingly, the biological activity of the best drug candidate was retained after adsorption at the surface of colloidal gold nanoparticles, broadening the options for clinical development.
• Molecular sugar bowl: γ-cyclodextrin with a disaccharide floor
  作者：Kazutaka Koga、Kanami Ishida、Tomonobu Yamada、De-Qi Yuan、Kahee Fujita

  DOI：10.1016/s0040-4039(98)02490-3

  日期：1999.1

  A series of molecular sugar bowls composed of a gamma-cyclodextrin wall and a trehalose floor have been synthesized by reacting 6A,6X-deoxy-6A,6X-dimercapto-gamma-cyclodextrin and 6,6'-deoxy-6,6'-diiodotrehalose. (C) 1999 Elsevier Science Ltd. All rights reserved.