UDP-L-Ara | 110222-42-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷酸
• 英文名称: UDP-L-Ara
• 英文别名: UDP-L-arabinopyranose；UDP-arabinose；[(2r,3s,4r,5r)-5-(2,4-Dioxo-3,4-Dihydropyrimidin-1(2h)-Yl)-3,4-Dihydroxytetrahydrofuran-2-Yl]methyl (2s,3r,4s,5s)-3,4,5-Trihydroxytetrahydro-2h-Pyran-2-Yl Dihydrogen Diphosphate；[[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl] hydrogen phosphate
• CAS: 110222-42-9
• 化学式: C₁₄H₂₂N₂O₁₆P₂
• 分子量: 536.28
• InChiKey: DQQDLYVHOTZLOR-YDXBSWQDSA-N

物化性质

• 密度：
  1.96±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -6.6
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  271
• 氢给体数：
  8
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  8-methoxycarbonyloctyl 2-acetamido-2-deoxy-β-D-glucopyranoside 、 UDP-L-Ara 在 β-galactosyltransferase 、 alkaline phosphatase 作用下， 以 various solvent(s) 为溶剂， 反应 18.0h， 以69%的产率得到methyl 9-[(2R,3R,4R,5S,6R)-3-acetamido-4-hydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxynonanoate
  参考文献：
  名称：

  Rapid Conversion of Unprotected Galactose Analogs to their Udp-Derivatives For Use in the Chemo-Enzymatic Synthesis of Unnatural Oligosaccharides

  摘要：

  The rapid conversion of D-galactose, its 2-deoxy, 3-deoxy, 4-deoxy and 6-deoxy derivatives and L-arabinose to their UDP-derivatives (2-7) is described. The procedure involves the in situ preparation of the per-O-trimethylsilylated glycopyranosyl iodides and their direct reaction with UDP. All six sugar nucleotides were active as substrates for beta(1-->4)-galactosyltransferase and were used to enzymatically prepare N-acetyllactosamine (8) and five of its analogs (9-13).

  DOI：

  10.1080/07328309808001892
• 作为产物：
  描述：

  L-(+)-arabinose 在 吡啶 、 碘代三甲硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 22.5h， 生成 UDP-L-Ara
  参考文献：
  名称：

  Rapid Conversion of Unprotected Galactose Analogs to their Udp-Derivatives For Use in the Chemo-Enzymatic Synthesis of Unnatural Oligosaccharides

  摘要：

  The rapid conversion of D-galactose, its 2-deoxy, 3-deoxy, 4-deoxy and 6-deoxy derivatives and L-arabinose to their UDP-derivatives (2-7) is described. The procedure involves the in situ preparation of the per-O-trimethylsilylated glycopyranosyl iodides and their direct reaction with UDP. All six sugar nucleotides were active as substrates for beta(1-->4)-galactosyltransferase and were used to enzymatically prepare N-acetyllactosamine (8) and five of its analogs (9-13).

  DOI：

  10.1080/07328309808001892

文献信息

• The biosynthesis of allelopathic di-C-glycosylflavones from the roots of Desmodium incanum (G. Mey.) DC
  作者：Bing Hao、John C. Caulfield、Mary L. Hamilton、John A. Pickett、Charles A. O. Midega、Zeyaur R. Khan、Junru R. Wang、Antony M. Hooper

  DOI：10.1039/c5ob01926e

  日期：——

  Biosynthesis of allelopathic di-C-glycosylflavones in the plant D. incanum, occurs by UDP-glucosylation of a natural or analogue 2-hydroxyflavonoid substrate, followed by a second glycosylation with UDP-Glu, UDP-Ara, or UDP-Gal.

  植物D. incanum中的抑制作用二-C-葡糖苷黄酮的生物合成发生在一个天然或类似的2-羟基黄酮底物上，首先通过UDP-葡糖基化，然后通过UDP-Glu、UDP-Ara或UDP-Gal进行第二次糖基化。
• Rapid Conversion of Unprotected Galactose Analogs to their Udp-Derivatives For Use in the Chemo-Enzymatic Synthesis of Unnatural Oligosaccharides
  作者：Taketo Uchiyama、Ole Hindsgaul

  DOI：10.1080/07328309808001892

  日期：1998.11

  The rapid conversion of D-galactose, its 2-deoxy, 3-deoxy, 4-deoxy and 6-deoxy derivatives and L-arabinose to their UDP-derivatives (2-7) is described. The procedure involves the in situ preparation of the per-O-trimethylsilylated glycopyranosyl iodides and their direct reaction with UDP. All six sugar nucleotides were active as substrates for beta(1-->4)-galactosyltransferase and were used to enzymatically prepare N-acetyllactosamine (8) and five of its analogs (9-13).