6-Amino-6-deoxy-L-galactonic acid | 169106-41-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: 6-Amino-6-deoxy-L-galactonic acid
• 英文别名: (2S,3R,4R,5S)-6-amino-2,3,4,5-tetrahydroxyhexanoic acid
• CAS: 169106-41-6
• 化学式: C₆H₁₃NO₆
• 分子量: 195.172
• InChiKey: CTWCTXWYMCZWOK-RSJOWCBRSA-N

物化性质

• 沸点：
  633.2±55.0 °C(Predicted)
• 密度：
  1.662±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.53
• 重原子数：
  13.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  144.24
• 氢给体数：
  6.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  (3S,4R,5S,6S)-6-(aminomethyl)oxane-2,3,4,5-tetrol 在 3,5-二硝基水杨酸 作用下， 反应 0.25h， 生成 6-Amino-6-deoxy-L-galactonic acid
  参考文献：
  名称：

  Substrate specificity of galactokinase from Streptococcus pneumoniae TIGR4 towards galactose, glucose, and their derivatives

  摘要：

  Galactokinases (GalKs) have attracted significant research attention for their potential applications in the enzymatic synthesis of unique sugar phosphates. The galactokinase (GalKSpe4) cloned from Streptococcus pneumoniae TIGR4 presents a remarkably broad substrate range including 14 diverse natural and unnatural sugars. TLC and MS studies revealed that GalKSpe4 had relaxed activity towards galactose derivatives with modifications on the C-6, 4- or 2-positions. Additionally, GalKSpe4 can also tolerate glucose while glucose derivatives with modifications on the C-6, 4- or 2-positions were unacceptable. More interestingly, GalKSpe4 can phosphorylate L-mannose in moderate yield (43%), while other L-sugars such as L-Gal cannot be recognized by this enzyme. These results are very significant because there is rarely enzyme reported that can phosphorylate such uncommon substrates as L-mannose. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.03.095

文献信息

• Aminopolyols from Carbohydrates: Amination of Sugars and Sugar‐Derived Tetrahydrofurans with Transaminases
  作者：Fabiana Subrizi、Laure Benhamou、John M. Ward、Tom D. Sheppard、Helen C. Hailes

  DOI：10.1002/anie.201813712

  日期：2019.3.18

  strategies. Demonstrated here is the reaction of TAms with sugar‐derived tetrahydrofuran (THF) aldehydes, obtained from the regioselective dehydration of biomass‐derived sugars, to provide access to cyclic aminodiols in high yields. In a preliminary study we have also established the direct transamination of sugars to give acyclic aminopolyols. Notably, the reaction of the ketose d‐fructose proceeds with

  碳水化合物是生物质的主要组成部分，由于其成本低、易于获得和立体化学多样性，作为化学品、材料和生物燃料的可持续来源具有独特的潜力。为了升级碳水化合物以获得有价值的含氮糖类化合物（例如氨基多元醇），使用转氨酶（TAms）的生物催化胺化已被研究作为传统合成策略的可持续替代方案。这里展示了 TAms 与糖衍生的四氢呋喃 (THF) 醛的反应，该醛是通过生物质衍生的糖的区域选择性脱水获得的，从而以高产率获得环状氨基二醇。在一项初步研究中，我们还建立了糖的直接转氨基作用以产生无环氨基多元醇。值得注意的是，酮糖d-果糖的反应以完全立体选择性进行，产生高纯度的有价值的氨基糖。