5-iodouridine-5'-diphosphate-α-D-N-acetylglucosamine | 1415556-30-7

• 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: 5-iodouridine-5'-diphosphate-α-D-N-acetylglucosamine
• 英文别名: [(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl] [[(2R,3S,4R,5R)-3,4-dihydroxy-5-(5-iodo-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl] hydrogen phosphate
• CAS: 1415556-30-7
• 化学式: C₁₇H₂₆IN₃O₁₇P₂
• 分子量: 733.255
• InChiKey: YROXCOIICAZRSR-IUXXHCEHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  300
• 氢给体数：
  9
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  5-iodouridine-5'-diphosphate-α-D-N-acetylglucosamine 、 5-醛基-2-噻吩硼酸 在 sodium tetrachloropalladate(II) 、 trisodium tris(3-sulfophenyl)phosphine 、 caesium carbonate 作用下， 以 水 为溶剂， 反应 2.0h， 以36%的产率得到5-(5-formylthien-2-yl)uridine-5'-diphosphate-α-D-N-acetylglucosamine
  参考文献：
  名称：

  优化 5 取代 UDP 糖的化学合成及其作为糖基转移酶抑制剂的评估。

  摘要：

  我们研究了焦磷酸键形成的不同化学方法对合成 5-取代 UDP-半乳糖和 UDP-N-乙酰氨基葡萄糖衍生物的适用性。使用磷吗啉化学，结合 N-甲基咪唑氯化物作为促进剂，被认为是制备这些非天然糖核苷酸的最可靠的合成方案。在这些条件下，主要合成目标 5-碘 UDP-半乳糖和 5-碘 UDP-N-乙酰氨基葡萄糖始终以 40-43% 的分离产率获得。两种 5-碘 UDP-糖都成功地用作 Suzuki-Miyaura 在水性条件下与 5-formylthien-2-ylboronic 酸交叉偶联的底物。重要的，

  DOI：

  10.1016/j.carres.2012.10.009
• 作为产物：
  描述：

  5-iodo-UDP-Glc 在 二磷酸酯 、 5-iodouridine-5'-diphosphate-α-D-galactose 、 glucose-1-phosphate uridylyltransferase 作用下， 以 aq. buffer 为溶剂， 反应 2.17h， 生成 5-iodouridine-5'-diphosphate-α-D-N-acetylglucosamine
  参考文献：
  名称：

  Enzymatic synthesis of nucleobase-modified UDP-sugars: scope and limitations

  摘要：

  Glucose-1-phosphate uridylyltransferase in conjunction with UDP-glucose pyrophosphorylase was found to catalyse the conversion of a range of 5-substituted UTP derivatives into the corresponding UDP-galactose derivatives in poor yield. Notably the 5-iodo derivative was not converted to UDP-sugar. In contrast, UDP-glucose pyrophosphorylase in conjunction with inorganic pyrophosphatase was particularly effective at converting 5-substituted UTP derivatives, including the iodo compound, into a range of gluco-configured 5-substituted UDP-sugar derivatives in good yields. Attempts to effect 400-epimerization of these 5-substituted UDP-glucose with UDP-glucose 4 ''-epimerase from yeast were unsuccessful, while use of the corresponding enzyme from Erwinia amylovora resulted in efficient epimerization of only 5-iodo-UDP-Glc, but not the corresponding 5-aryl derivatives, to give 5-iodo-UDP-Gal. Given the established potential for Pd-mediated cross-coupling of 5-iodo-UDP-sugars, this provides convenient access to the galacto-configured 5-substituted-UDP-sugars from gluco-configured substrates and 5-iodo-UTP. (C) 2015 The Authors. Published by Elsevier Ltd.

  DOI：

  10.1016/j.carres.2014.12.005