D-glucopyranosyl β,β-disulphide | 54495-24-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: D-glucopyranosyl β,β-disulphide
• 英文别名: 1,1-dithio-β-diglucopyranoside；β-thioglucose disulfide；1,1'-dithiobis(β-D-glucopyranoside)；bis(1-thio-b-D-glucopyranosyl)1,1'-disulfide；D-Glcp-βS(1->1')Sβ-D-Glcp；di-β-D-glucopyranosyl disulfide；Di-β-D-glucopyranosyl-disulfid；(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]disulfanyl]oxane-3,4,5-triol
• CAS: 54495-24-8
• 化学式: C₁₂H₂₂O₁₀S₂
• 分子量: 390.433
• InChiKey: KBTDRQVARMJBHT-NCFXGAEVSA-N

物化性质

• 沸点：
  734.1±60.0 °C(Predicted)
• 密度：
  1.81±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.4
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  231
• 氢给体数：
  8
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 D-glucopyranosyl β,β-disulphide 反应 15.0h， 生成 bis(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)disulfide
  参考文献：
  名称：

  Formation of Disulphide Links by Dioxysulphonium-Oxidation

  摘要：

  p-Toluenesulphonyl chloride has been used to oxidise thiols, including 1-thio-beta-D-glucopyranose, or their sodium salts, to disulphides.

  DOI：

  10.1080/00397919308011205
• 作为产物：
  描述：

  1,2,3,4,6-alpha-D-葡萄糖五乙酸酯 在 ammonium hydroxide 、 N-碘代丁二酰亚胺 、 氢溴酸 、 碘 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 、 乙腈 为溶剂， 反应 18.0h， 生成 D-glucopyranosyl β,β-disulphide
  参考文献：
  名称：

  A Sweet H₂S/H₂O₂ Dual Release System and Specific Protein S-Persulfidation Mediated by Thioglucose/Glucose Oxidase

  摘要：

  DOI：

  10.1021/jacs.1c06372

文献信息

• Novel methods for the delivery of polynucleotides to cells
  申请人：——

  公开号：US20030235916A1

  公开（公告）日：2003-12-25

  Process are described for the delivery of a polynucleotide to a cell. The process comprises forming a salt stable complex between the polynucleotide and a cationic surfactant. Ternary complexes are also made by associating an amphipathic compound with the binary complex. The resultant complexes are suitable for delivery of the polynucleotide to cells in vitro and in vivo.

  描述了将多核苷酸传递到细胞的过程。该过程包括在多核苷酸和阳离子表面活性剂之间形成一个盐稳定的复合物。三元复合物也可以通过将一个两性化合物与二元复合物结合而制备。所得的复合物适用于体外和体内向细胞传递多核苷酸。
• Phosphine-mediated disulfide metathesis in aqueous media
  作者：Rémi Caraballo、Morakot Sakulsombat、Olof Ramström

  DOI：10.1039/c0cc03622f

  日期：——

  Dynamic carbohydrate systems have been efficiently generated through phosphine-mediated disulfide metathesis in aqueous media. The protein compatibility and binding features of the dynamic systems were demonstrated in situ using 1H STD NMR.

  通过磷化物介导的二硫化物易位反应，在水性介质中高效合成了动态碳水化合物系统。通过使用1H STD NMR在原位展示了这些动态系统的蛋白质兼容性和结合特性。
• A straightforward synthetic access to symmetrical glycosyl disulfides and biological evaluation thereof
  作者：Matteo Adinolfi、Domenica Capasso、Sonia Di Gaetano、Alfonso Iadonisi、Loredana Leone、Antonello Pastore

  DOI：10.1039/c1ob05619k

  日期：——

  Symmetrical glycosyl disulfides can be prepared within a few hours from per-O-acetylated precursors via a sequential approach entailing short reactions and no purification of any intermediate. The final thiolate-to-disulfide oxidation step is noticeably accelerated by low amounts of phenyl diselenide under air. Applicability of the strategy to non-saccharidic symmetrical alkyl disulfides has also been examined. A preliminary assay of the cytotoxic activity of symmetrical 1,1′- disulfides was performed on two human tumor cell lines, and a noteworthy activity was recorded for a range of these synthetic compounds.

  对称的糖基二硫化物可以通过连续反应方法，在几小时内从全乙酰化前体制备得到，期间无需对任何中间体进行纯化。在最后的硫醇盐氧化成二硫化物步骤中，少量的二苯基二硒化物在空气中能显著加速反应。这个策略对非糖类的对称烷基二硫化物的适用性也进行了研究。对一系列合成的1,1'-二硫化物在两种人类肿瘤细胞系上进行了初步的细胞毒性活性测试，结果表明这些化合物具有显著的活性。
• Metal-free synthesis of imino-disaccharides and calix-iminosugars by photoinduced radical thiol–ene coupling (TEC)
  作者：Renaud Zelli、Pascal Dumy、Alberto Marra

  DOI：10.1039/d0ob00198h

  日期：——

  Deprotected iminosugar alkenes were subjected to thiol–ene coupling with deprotected sugar thiols to afford new imino-disaccharides. Two thiol–ene couplings converted these alkenes into iminosugar thiols and then multivalent iminosugars.

  去保护基的亚胺糖烯经过巯基-烯烃偶联反应与去保护基的糖巯基反应，形成新的亚胺二糖。经过两次巯基-烯烃偶联反应，这些烯烃转化为亚胺糖巯基，进而形成多价亚胺糖。
• Chemoselective Solution- and Solid-Phase Synthesis of Disulfide-Linked Glycopeptides
  作者：Katreen A. F. Banisalman、Athina Polykandritou、Francis M. Barnieh、Goreti Ribeiro Morais、Robert A. Falconer

  DOI：10.1021/acs.joc.2c01651

  日期：2022.11.4

  glycopeptides. Acetate-protected glycosylsulfenyl hydrazines are shown to be highly reactive with the thiol group of cysteine residues within peptides, both in solution and as part of conventional solid-phase peptide synthesis protocols. The efficiency of this glycosylation methodology with unprotected carbohydrates is also demonstrated, which avoids the need for deprotection steps and further extends its utility

  肽和蛋白质的糖基化是一种广泛采用的策略，用于模拟重要的翻译后修饰或调节肽的物理化学特性以增强其递送。此外，糖基化通过硫原子赋予所得糖缀合物更高的化学和代谢稳定性。在此，我们报告了一种简单且具有化学选择性的程序来制备二硫键连接的糖肽。乙酸盐保护的糖基亚磺酰肼被证明与肽中半胱氨酸残基的硫醇基团具有高度反应性，无论是在溶液中还是作为常规固相肽合成方案的一部分。还证明了这种使用未保护碳水化合物的糖基化方法的效率，它避免了脱保护步骤的需要并进一步扩展了它的实用性，二硫键连接的糖肽以极好的产量产生。鉴于糖基化肽在结构糖生物学、药理学和治疗学中的重要性，