N6-tert-butoxycarbonyl-5'-deoxy-5'-N-[(ethenyl)sulfonyl]amino-2',3'-O-isopropylideneadenosine | 942509-00-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: N6-tert-butoxycarbonyl-5'-deoxy-5'-N-[(ethenyl)sulfonyl]amino-2',3'-O-isopropylideneadenosine
• 英文别名: N⁶-tert-butoxycarbonyl-5'-deoxy-5'-N-[(ethenyl)sulfonyl]amino-2',3'-O-isopropylideneadenosine；5'-deoxy-5'-N-[(ethenyl)sulfonyl]amino-2',3'-O-isopropylidene-adenosine
• CAS: 942509-00-4
• 化学式: C₂₀H₂₈N₆O₇S
• 分子量: 496.544
• InChiKey: KRUJOGSACYNYBQ-LSCFUAHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.65
• 重原子数：
  34.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  155.79
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  N6-tert-butoxycarbonyl-5'-deoxy-5'-N-[(ethenyl)sulfonyl]amino-2',3'-O-isopropylideneadenosine 在 bis-triphenylphosphine-palladium(II) chloride 三乙胺 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.5h， 生成 (E)-5'-deoxy-5'-N-({[2-(2-hydroxyphenyl)ethenyl]sulfonyl}amino)adenosine
  参考文献：
  名称：

  A Mechanism-Based Aryl Carrier Protein/Thiolation Domain Affinity Probe

  摘要：

  The design, synthesis, and biochemical characterization of a mechanism-based aryl carrier protein (ArCP) affinity probe that selectively modifies the terminal thiol of the aryl carrier protein phosphopantetheine (Ppant) prosthetic group is described. Labeling of the aryl carrier protein was shown to require the cognate adenylating enzyme to channel the affinity probe onto the Ppant cofactor. The selective labeling was established by observation of the phosphopantetheinyl ejection ion via MS/MS, and the probe was also found to stabilize an interaction between an aryl carrier protein and adenylating enzyme by an electrophoretic mobility shift assay.

  DOI：

  10.1021/ja069201e
• 作为产物：
  描述：

  5'-azido-5'-deoxy-2',3'-O-isopropylidene adenosine 在 palladium on activated charcoal TEA 、 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 20.0 ℃ 、253.33 kPa 条件下， 反应 8.5h， 生成 N6-tert-butoxycarbonyl-5'-deoxy-5'-N-[(ethenyl)sulfonyl]amino-2',3'-O-isopropylideneadenosine
  参考文献：
  名称：

  A Mechanism-Based Aryl Carrier Protein/Thiolation Domain Affinity Probe

  摘要：

  The design, synthesis, and biochemical characterization of a mechanism-based aryl carrier protein (ArCP) affinity probe that selectively modifies the terminal thiol of the aryl carrier protein phosphopantetheine (Ppant) prosthetic group is described. Labeling of the aryl carrier protein was shown to require the cognate adenylating enzyme to channel the affinity probe onto the Ppant cofactor. The selective labeling was established by observation of the phosphopantetheinyl ejection ion via MS/MS, and the probe was also found to stabilize an interaction between an aryl carrier protein and adenylating enzyme by an electrophoretic mobility shift assay.

  DOI：

  10.1021/ja069201e

文献信息

• Antibacterial Agents
  申请人：Aldrich Courtney

  公开号：US20080293666A1

  公开（公告）日：2008-11-27

  The invention provides compounds of formula (I) and salts thereof: R 1 -L-R 2 —B wherein R 1 , L, R 2 , and B have any of the values defined herein, as well as compositions comprising such compounds, and therapeutic methods comprising the administration of such compounds or salts. The compounds block siderophore production in bacteria and are useful as antibacterial agents.

  这项发明提供了化合物的公式(I)及其盐：R1-L-R2—B，其中R1、L、R2和B具有本文中定义的任何值，以及包含这种化合物的组合物，以及包含这种化合物或盐的治疗方法。这些化合物可以阻断细菌中的铁载体产生，并可用作抗菌剂。