GDP-2-deoxy-α-D-glucose

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷酸
• 英文名称: GDP-2-deoxy-α-D-glucose
• 英文别名: guanosine-5’-diphospho-2′′-deoxy-α-D-glucopyranosyl；[[(2R,3S,4R,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl] hydrogen phosphate
• 化学式: C₁₆H₂₅N₅O₁₅P₂
• 分子量: 589.347
• InChiKey: VVDQMBZYGGWECU-CNFIAULHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.3
• 重原子数：
  38
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  307
• 氢给体数：
  9
• 氢受体数：
  17

反应信息

• 作为产物：
  描述：

  2-deoxy-α-D-glucose 1-phosphate 、 GTP 在 GDP-mannose pyrophosphorylase 、 Tris buffer 、 magnesium chloride 作用下， 以 水 为溶剂， 反应 0.08h， 生成 GDP-2-deoxy-α-D-glucose
  参考文献：
  名称：

  The preparation of deoxy derivatives of mannose-1-phosphate and their substrate specificity towards recombinant GDP-mannose pyrophosphorylase from Salmonella enterica, group B

  摘要：

  2-Deoxy-alpha-D-glucose-1-phosphate, 3-deoxy-alpha-D-arabino-hexose-1-phosphate, 4-deoxy-alpha-D-lyxo-hexose-1-phosphate, and alpha-D-lyxose-1-phosphate were synthesised chemically, and evaluated as substrates for a recombinant GDP-mannose pyrophosphorylase (Salmonella enterica, group B, cloned in Escherichia coli). The deoxy derivatives were all substrates for the enzyme, with slightly reduced V-max values but significantly higher K-m values than those recorded for the native substrate, mannose-1-phosphate. The pyrophosphorylase was used for the synthesis of GDP-mannose analogues GDP-2-deoxy-glucose and GDP-lyxose on a milligram scale. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00556-x

文献信息

• Efficient Enzymatic Synthesis of Guanosine 5′-Diphosphate-Sugars and Derivatives
  作者：Lei Li、Yonghui Liu、Yue Wan、Yanhong Li、Xi Chen、Wei Zhao、Peng George Wang

  DOI：10.1021/ol402585c

  日期：2013.11

  Bifidobacterium infantis (NahK_15697), a guanosine 5′-diphosphate (GDP)-mannose pyrophosphorylase from Pyrococcus furiosus (PFManC), and an Escherichia coli inorganic pyrophosphatase (EcPpA) were used efficiently for a one-pot three-enzyme synthesis of GDP-mannose, GDP-glucose, their derivatives, and GDP-talose. This study represents the first facile and efficient enzymatic synthesis of GDP-sugars and derivatives

  来自婴儿双歧杆菌的N-乙酰己糖胺 1-激酶(NahK_15697)、来自激烈火球菌(PFManC)的鸟苷 5'-二磷酸 (GDP)-甘露糖焦磷酸化酶和大肠杆菌无机焦磷酸酶 (EcPpA) 被有效地用于一锅GDP-甘露糖、GDP-葡萄糖及其衍生物和GDP-塔糖的三酶合成。这项研究代表了从单糖和衍生物开始的 GDP 糖和衍生物的首次简便有效的酶促合成。