4-azido-4-deoxy-D-galactose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-azido-4-deoxy-D-galactose
• 英文别名: 4-Azido-4-deoxy-d-galactose；(3R,4S,5R,6S)-5-azido-6-(hydroxymethyl)oxane-2,3,4-triol
• 化学式: C₆H₁₁N₃O₅
• 分子量: 205.17
• InChiKey: UMVGRQGCOVIFLI-SVZMEOIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  105
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-azido-4-deoxy-D-galactose 在 Streptococcus pneumoniae TIGR₄ galactokinase 、 5’-三磷酸腺苷 、 magnesium chloride 作用下， 反应 20.0h， 生成
  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
• 作为产物：
  描述：

  methyl 2,3,6-tri-O-benzoyl-α-D-glucopyranoside 在 吡啶 、 sodium azide 、 硫酸 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.5h， 生成 4-azido-4-deoxy-D-galactose
  参考文献：
  名称：

  大肠杆菌半乳糖激酶的底物特异性研究。

  摘要：

  体外糖随机化（IVG）技术取决于快速合成糖磷酸酯的能力。与化学合成相比，酶促（激酶）途径转化为糖磷酸酯对于该应用而言将是有吸引力的。这项工作专注于高通量比色半乳糖激酶（GalK）检测方法的开发及其在探测大肠杆菌GalK的底物特异性和动力学参数方面的应用。证明的二硝基水杨酸测定法也应普遍适用于多种糖加工酶。[反应：看文字]

  DOI：

  10.1021/ol034642d

文献信息

• Preparation and properties of some photolabile sugar derivatives for affinity labelling
  作者：Gerhart Kurz、Jochen Lehmann、Roland Thieme

  DOI：10.1016/0008-6215(85)85191-0

  日期：1985.2

  Abstract Sugar derivatives carrying various photolabile groups at various positions have been synthesised, namely, 4-azido-4-deoxy- d -galactose, 4-azi-4-deoxy- d -xylo-hexopyranose (4), 3,7-anhydro-2-azi-1,2-dideoxy- d -glycero- l -manno-octitol (6), and 3-azi-1-methoxybutyl β- d -glucopyranoside (8), and 4-(2-diazo-3,3,3-trifluoropropionyl)- d -glucose. They were tested for their applicability in

  摘要合成了在不同位置带有不同光不稳定基团的糖衍生物，即4-叠氮基4-脱氧-d-半乳糖，4-叠氮基4-脱氧-d-木糖己糖（4），3,7-脱水-2-azi-1,2-二脱氧-d-甘油-1-甘露辛醇（6）和3-azi-1-甲氧基丁基β-d-吡喃葡萄糖苷（8）和4-（2-重氮-3 ，3，3-三氟丙酰基）-d-葡萄糖。对它们在糖结合蛋白的光亲和标记中的适用性进行了测试，使用重氮基衍生物4、6和8获得了最佳的照射波长和光解衰减速率的结果。
• Biosynthesis of nucleotide sugars by a promiscuous UDP-sugar pyrophosphorylase from Arabidopsis thaliana (AtUSP)
  作者：Jun Liu、Yang Zou、Wanyi Guan、Yafei Zhai、Mengyang Xue、Lan Jin、Xueer Zhao、Junkai Dong、Wenjun Wang、Jie Shen、Peng George Wang、Min Chen

  DOI：10.1016/j.bmcl.2013.04.090

  日期：2013.7

  Nucleotide sugars are activated forms of monosaccharides and key intermediates of carbohydrate metabolism in all organisms. The availability of structurally diverse nucleotide sugars is particularly important for the characterization of glycosyltransferases. Given that limited methods are available for preparation of nucleotide sugars, especially their useful non-natural derivatives, we introduced herein an efficient one-step three-enzyme catalytic system for the synthesis of nucleotide sugars from monosaccharides. In this study, a promiscuous UDP-sugar pyrophosphorylase (USP) from Arabidopsis thaliana (AtUSP) was used with a galactokinase from Streptococcus pneumoniae TIGR4 (SpGalK) and an inorganic pyrophosphatase (PPase) to effectively synthesize four UDP-sugars. AtUSP has better tolerance for C4-derivatives of Gal-1-P compared to UDP-glucose pyrophosphorylase from S. pneumoniae TIGR4 (SpGalU). Besides, the nucleotide substrate specificity and kinetic parameters of AtUSP were systematically studied. AtUSP exhibited considerable activity toward UTP, dUTP and dTTP, the yield of which was 87%, 85% and 84%, respectively. These results provide abundant information for better understanding of the relationship between substrate specificity and structural features of AtUSP. (C) 2013 Elsevier Ltd. All rights reserved.