D-gluconothionolactam | 128732-72-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: D-gluconothionolactam
• 英文别名: (3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)piperidine-2-thione
• CAS: 128732-72-9
• 化学式: C₆H₁₁NO₄S
• 分子量: 193.224
• InChiKey: QTZRMTCOLWERQB-SQOUGZDYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  125
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  D-gluconothionolactam 在 氨 作用下， 以 甲醇 为溶剂， 反应 11.0h， 生成 D-glucoamidine
  参考文献：
  名称：

  Papandreou; Tong; Ganem, Journal of the American Chemical Society, 1993, vol. 115, # 25, p. 11682 - 11690

  摘要：

  DOI：
• 作为产物：
  描述：

  β-6,6-<1H>-nojirimycin 在 劳森试剂 、 吡啶 、 盐酸 、 sodium hydroxide 、 碘 、 六甲基二硅氮烷 、 potassium iodide 作用下， 以 甲醇 、 苯 为溶剂， 反应 26.58h， 生成 D-gluconothionolactam
  参考文献：
  名称：

  Papandreou; Tong; Ganem, Journal of the American Chemical Society, 1993, vol. 115, # 25, p. 11682 - 11690

  摘要：

  DOI：

文献信息

• Concise synthesis of glyconoamidines as affinity ligands for the purification of β-glucosidase involved in control of some biological events including plant leaf movement
  作者：Eisuke Kato、Tadahiro Kumagai、Minoru Ueda

  DOI：10.1016/j.tetlet.2005.05.060

  日期：2005.7

  biochemical studies and would be useful as an affinity ligand for purification of glycosidase. However, its use for the specific inhibition of glucosidase which is highly specific to a glycoside with voluntary aglycon is seriously restricted because no universal method for the synthesis of N-alkylated glyconoamidine has been reported. Here, we report a concise synthesis of N-alkylated Ganem’s glyconoamidine

  糖苷酶通过生物有趣的过程参与某些内源性生物活性物质的失活或储存。例如，通过生物钟通过β-葡萄糖苷酶活性的调节来控制夜蛾叶片的运动。Ganem的糖氨（1）在生化研究中用作葡糖苷酶的微摩尔抑制剂，可用作糖苷酶纯化的亲和配体。但是，由于没有报道用于合成N-烷基化的糖氨am的通用方法，因此严重限制了其对对具有自愿糖苷配基的糖苷高度特异性的葡糖苷酶的特异性抑制的用途。在这里，我们报告N的简明综合使用未保护的糖衍生物，用自愿糖苷酸将Ganem's糖氨am酸烷基化。
• Affinity purification and characterization of a key enzyme responsible for circadian rhythmic control of nyctinasty in Lespedeza cuneata L
  作者：Eisuke Kato、Takehiko Sasaki、Minoru Ueda

  DOI：10.1016/j.bmc.2008.02.035

  日期：2008.4

  The synthesis of an affinity gel aimed at leaf-opening factor beta-glucosidase (LOFG) and affinity purification of LOFG is presented. A gluconamidine-based beta-glucosidase inhibitor was used as the ligand of the affinity gel. beta-Glucosidase exhibiting an activity shift throughout the day was selectively purified from Lespedeza cuneata Don by the affinity gel. The resulting LOFG exhibited high substrate specificity toward the leaf-opening factor. (c) 2008 Elsevier Ltd. All rights reserved.
• Affinity purification of the key enzyme of nyctinasty controlling the rhythm of leaf movement using gluconamidine ligand
  作者：Eisuke Kato、Takehiko Sasaki、Tadahiro Kumagai、Minoru Ueda

  DOI：10.1016/j.tetlet.2007.01.085

  日期：2007.3

  Synthesis of affinity get aimed for leaf-opening factor beta-glucosidase (LOFG) and affinity purification of LOFG are presented. Gluconamidine-based beta-glucosidase inhibitor was utilized for the ligand of the affinity gel. beta-Glucosidase exhibiting activity shift throughout the day was selectively purified from Lespedeza cuneata Don by the affinity gel. The resulting LOFG exhibited a high substrate specificity toward the leaf-opening factor. (c) 2007 Published by Elsevier Ltd.
• Mimicking the glucosidase transition state: shape/charge considerations
  作者：Bruce Ganem、George Papandreou

  DOI：10.1021/ja00023a078

  日期：1991.11
• Potent, broad-spectrum inhibition of glycosidases by an amidine derivative of D-glucose
  作者：Michael K. Tong、George Papandreou、Bruce Ganem

  DOI：10.1021/ja00172a045

  日期：1990.8