bis(1-deoxy-2,3:4,5-di-O-isopropylidene-β-D-fructopyranos-1-yl) disulfide | 128333-80-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: bis(1-deoxy-2,3:4,5-di-O-isopropylidene-β-D-fructopyranos-1-yl) disulfide
• 英文别名: bis(2,3:4,5-di-O-isopropylidene-1-deoxy-β-D-fructopyranos-1-yl)disulfide；(1R,2S,6R,9R)-4,4,11,11-tetramethyl-6-[[[(1R,2S,6R,9R)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-6-yl]methyldisulfanyl]methyl]-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecane
• CAS: 128333-80-2
• 化学式: C₂₄H₃₈O₁₀S₂
• 分子量: 550.692
• InChiKey: YGKGRJJDXGHESF-AGLGUODFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.16
• 重原子数：
  36.0
• 可旋转键数：
  5.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  92.3
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为产物：
  描述：

  2,3:4,5-di-O-isopropylidene-1-O-(trifluoromethanesulfonyl)-β-D-fructopyranose 在 sodium methylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 23.58h， 生成 bis(1-deoxy-2,3:4,5-di-O-isopropylidene-β-D-fructopyranos-1-yl) disulfide
  参考文献：
  名称：

  1-（叠氮芳基）酰胺基和1-（叠氮芳基）硫基-1-脱氧-d-果糖类似物的制备

  摘要：

  合成d'azido-4N-β-D-果糖吡喃糖基羟基-2苯甲酰胺，de S- [azido-4硝基-2苯基] -1 thio-1果糖吡喃糖等和部分d'azido-1 desoxy-1二-“ O”-异亚丙基-2,3：4,5果糖吡喃糖等。N-羟基琥珀酰亚胺二酰胺叠氮基4羟基-2苯甲酸酯（ou d'azido-1氟4硝基3苯）及巯基乙酸钾

  DOI：

  10.1016/0008-6215(89)85100-6

文献信息

• Synthesis and membranoprotective properties of new disulfides with monoterpene and carbohydrate fragments
  作者：S. V. Pestova、E. S. Izmest´ev、O. G. Shevchenko、S. A. Rubtsova、A. V. Kuchin

  DOI：10.1007/s11172-015-0926-2

  日期：2015.3

  A cooxidation of carbohydrate and terpene thiols gives mixtures of disulfides containing 51—90% of the unsymmetric product. Membranoprotective and antioxidant properties of obtained unsymmetric and symmetric disulfides were evaluated based on their ability to inhibit the H2O2-induced hemolysis of erythrocytes, as well as the accumulation of secondary products of the peroxy oxidation of lipids and the

  碳水化合物和萜烯硫醇的共氧化产生含有 51-90% 不对称产物的二硫化物混合物。获得的不对称和对称二硫化物的膜保护和抗氧化性能根据它们抑制 H2O2 诱导的红细胞溶血的能力以及脂质过氧氧化和血红蛋白氧化的次级产物积累的能力进行评估。
• Synthesis and inhibitory activity of substrate-analog fructosyl peptide oxidase inhibitors
  作者：Bunta Watanabe、Atsushi Ichiyanagi、Kozo Hirokawa、Keiko Gomi、Toru Nakatsu、Hiroaki Kato、Naoki Kajiyama

  DOI：10.1016/j.bmcl.2015.07.045

  日期：2015.9

  Fructosyl peptide oxidases (FPOXs) play a crucial role in the diagnosis of diabetes. Their main function is to cleave fructosyl amino acids or fructosyl peptides into glucosone and the corresponding amino acids/dipeptides. In this study, the substrate-analog FPOX inhibitors 1a-c were successfully designed and synthesized. These inhibitors mimic N-alpha-fructosyl-L-valine (Fru-Val), [N-alpha-fructosyl-L-valyl]-L-histidine (Fru-ValHis), and N-epsilon-fructosyl-L-lysine (epsilon Fru-Lys), respectively. The secondary nitrogen atom in the natural substrates, linking fructose and amino acid or dipeptide moieties, was substituted in 1a-c with a sulfur atom to avoid enzymatic cleavage. Kinetic studies revealed that 1a-c act as competitive inhibitors against an FPOX obtained from Coniochaeta sp., and K-i values of 11.1, 66.8, and 782 mu M were obtained for 1a-c, respectively. (C) 2015 Elsevier Ltd. All rights reserved.
• GOODWIN, JAMES C., CARBOHYDR. RES., 195,(1989) N, C. 150-156
  作者：GOODWIN, JAMES C.

  DOI：——

  日期：——