tert-butyl 6-O-[4,6-bis-O-(4-bromobenzoyl)-β-D-glucopyranosyl]-β-D-glucopyranoside | 1022927-17-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl 6-O-[4,6-bis-O-(4-bromobenzoyl)-β-D-glucopyranosyl]-β-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5R,6R)-3-(4-bromobenzoyl)oxy-4,5-dihydroxy-6-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(2-methylpropan-2-yl)oxy]oxan-2-yl]methoxy]oxan-2-yl]methyl 4-bromobenzoate
• CAS: 1022927-17-8
• 化学式: C₃₀H₃₆Br₂O₁₃
• 分子量: 764.416
• InChiKey: RSWCGZZLZZURED-TXMNWJTCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  45
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  191
• 氢给体数：
  5
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  gentiobiose hepta-acetate 在 吡啶 、 甲醇 、 4-二甲氨基吡啶 、 三氟化硼乙醚 、 sodium methylate 、 对甲苯磺酸 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 tert-butyl 6-O-[4,6-bis-O-(4-bromobenzoyl)-β-D-glucopyranosyl]-β-D-glucopyranoside
  参考文献：
  名称：

  Synthetic menthyl α/β-(1→6)-diglucopyranosides-induced cell death in human leukemia cells is dependent on caspases

  摘要：

  A series of alkyl alpha/beta-(1 -> 6)-diglucopyranosides 1-12 were synthesized and assessed for cytotoxicity against HL-60, U937, Molt-3 and MCF-7 cancer cell lines. The menthyl derivatives displayed strong cytotoxic properties showing IC50 values between 6 and 16 mu M. Furthermore, we demonstrated that the selected synthetic (+)-menthyl beta-(1 -> 6)-diglucopyranoside 5 induces apoptotic cell death in human leukemia cells through a mechanism that involves activation of multiple caspases. Cell death was completely prevented by the non-specific caspase inhibitor z-VAD-fmk and found to be associated with the release of cytochrome c, an increase in the expression of Bax levels and a decrease in the generation of reactive oxygen species. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.035

文献信息

• Conformational Domino Effect in Saccharides: A Prediction from Alkyl β-(1→6)-Diglucopyranosides
  作者：Alfredo Roën、Juan I. Padrón、Carlos Mayato、Jesús T. Vázquez

  DOI：10.1021/jo800191z

  日期：2008.5.1

  that the rotational properties of the interglycosidic linkage depend on the structural natures of both the aglycon and the solvent. Stereoelectronic and steric factors explain this rotational dependence, the gauche−trans (gt) rotamer being the most stable. Furthermore, correlations between Taft’s steric parameters or between the pKa values of the alkyl substituent (aglycon) versus corresponding rotamer

  合成了一系列含有非手性和手性糖苷配基的烷基β- d-吡喃葡萄糖基- （1→6）-β- d-吡喃葡糖苷，并通过NMR和CD进行了分析。从四组二糖中收集的结果表明，糖苷间键的旋转特性取决于糖苷配基和溶剂的结构性质。立体电子和空间因素解释了这种旋转依赖性，其中gauche - trans（gt）旋转异构体是最稳定的。此外，塔夫脱（Taft）空间参数之间或p K a之间的相关性观察到烷基取代基（糖苷配基）相对于相应的旋转异构体群体的值。这些结果表明寡糖具有天然的构象多米诺效应，其中每个（1→6）糖苷间键的构象特性将取决于先前残基或其糖苷配基的结构。另外，观察到残基II上的羟甲基对残基I上的糖苷配基的非常弱的旋转种群依赖性。gauche - gauche（gg）rotamer的种群减少，而gt的种群随着远端糖苷配基的Taft立体参数的增加而增加，而与二糖系列和溶剂无关。
• Synthetic menthyl α/β-(1→6)-diglucopyranosides-induced cell death in human leukemia cells is dependent on caspases
  作者：María Teresa Marrero、Sara Tejera、Sara Estévez、José Quintana、Carlos Mayato、Rosa L. Dorta、Jesús T. Vázquez、Francisco Estévez

  DOI：10.1016/j.bmcl.2012.04.035

  日期：2012.6

  A series of alkyl alpha/beta-(1 -> 6)-diglucopyranosides 1-12 were synthesized and assessed for cytotoxicity against HL-60, U937, Molt-3 and MCF-7 cancer cell lines. The menthyl derivatives displayed strong cytotoxic properties showing IC50 values between 6 and 16 mu M. Furthermore, we demonstrated that the selected synthetic (+)-menthyl beta-(1 -> 6)-diglucopyranoside 5 induces apoptotic cell death in human leukemia cells through a mechanism that involves activation of multiple caspases. Cell death was completely prevented by the non-specific caspase inhibitor z-VAD-fmk and found to be associated with the release of cytochrome c, an increase in the expression of Bax levels and a decrease in the generation of reactive oxygen species. (C) 2012 Elsevier Ltd. All rights reserved.