methyl 5-Iodo-α-D-arabinofuranoside | 281678-21-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 5-Iodo-α-D-arabinofuranoside
• 英文别名: (2S,3S,4S,5S)-2-(iodomethyl)-5-methoxyoxolane-3,4-diol
• CAS: 281678-21-5
• 化学式: C₆H₁₁IO₄
• 分子量: 274.055
• InChiKey: WYMYPTFVMQUWRR-ZXXMMSQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  11
• 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：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  、 methyl 5-Iodo-α-D-arabinofuranoside 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以28%的产率得到ethyl 2-(methyl 5-thio-α-D-arabinofuranoside-5-S-yl)acetamido-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate
  参考文献：
  名称：

  Design, Synthesis, and X-ray Analysis of a Glycoconjugate Bound to Mycobacterium tuberculosis Antigen 85C

  摘要：

  Tuberculosis (TB) is a global health threat with nearly 500 000 new cases of multidrug-resistant TB estimated to occur every year, so new drugs are desperately needed. A number of current antimycobacterial drugs work by interfering with the biosynthesis of key components of the mycolylar-abinogalactan (mAG). In light of this observation, other enzymes involved in the synthesis of the mAG should also serve as targets for antimycobacterial drug development. One potential target is the Antigen 85 (Ag85) complex, a family of mycolyltransferases that are responsible for the transfer of mycolic acids from trehalose monomycolate (TMM) to the arabinogalactan. Virtual thiophenyl arabinoside conjugates were docked to antigen Ag85C (PDB code: 1va5) using Glide. Compounds with good docking scores were synthesized by a Gewald synthesis followed by linking to 5-thioarabinofuranosides. The resulting thiophenyl-thioarabinofuranosides were assayed for inhibition of mycoyltransferase activity using a 4-methylumbelliferyl butyrate fluorescence assay. The conjugates showed K-i values ranging from 18.2 to 71.0 mu M. The most potent inhibitor was soaked into crystals of Mycobacterium tuberculosis antigen 85C and the structure of the complex determined. The X-ray structure shows the compound bound within the active site of the enzyme with the thiophene moiety positioned in the putative alpha-chain binding site of TMM and the arabinofuranoside moiety within the known carbohydrate-binding site as exhibited for the Ag85B-trehalose crystal structure. Unexpectedly, no specific hydrogen bonding interactions are being formed between the arabinofuranoside and the carbohydrate-binding site of the active site suggesting that the binding of the arabinoside within this structure is driven by shape complementarily between the arabinosyl moiety and the carbohydrate binding site.

  DOI：

  10.1021/bc3004342
• 作为产物：
  描述：

  methyl D-arabinofuranoside 在 吡啶 、 sodium iodide 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 methyl 5-Iodo-α-D-arabinofuranoside
  参考文献：
  名称：

  未保护的甲基呋喃糖苷和吡喃糖苷中伯醇向碘化物的区域选择性转化

  摘要：

  描述了用碘化物对甲基糖苷中的伯羟基进行区域选择性置换的两种方法。第一种方法是使用三苯膦和碘对文献程序的改进，其中纯化在反相柱上进行，以便有效地从三苯膦氧化物中分离出所需的碘苷。第二种方法采用了一种新的方法，即在吡啶中用空间位阻的 2,4,6-三氯和 2,4,6-三溴苯磺酰氯进行磺酰化。如此形成的磺酸盐是有效的离去基团，并且可以在一锅法中进行碘化物的取代。碘苷的保护也描述为用三氯乙酰亚胺苄酯苄基化或用三乙基甲硅烷基氯甲硅烷基化。

  DOI：

  10.1055/s-2002-33641