2-azidoethyl 5-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-2,3-di-O-tert-butyldimethylsilyl-α-D-arabinofuranoside | 330983-82-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-azidoethyl 5-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-2,3-di-O-tert-butyldimethylsilyl-α-D-arabinofuranoside
• 英文别名: [(2R,3R,4S,5S)-5-[[(2R,3R,4S,5S)-5-(2-azidoethoxy)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]oxolan-2-yl]methoxy]-3,4-dibenzoyloxyoxolan-2-yl]methyl benzoate
• CAS: 330983-82-9
• 化学式: C₄₅H₆₁N₃O₁₂Si₂
• 分子量: 892.163
• InChiKey: LFAICWGOBSLWRC-VEQQERDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.87
• 重原子数：
  62
• 可旋转键数：
  23
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  149
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  2-azidoethyl 5-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-2,3-di-O-tert-butyldimethylsilyl-α-D-arabinofuranoside 在 三苯基膦 作用下， 以 水 、 苯 为溶剂， 反应 6.0h， 以87%的产率得到2-aminoethyl 5-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-2,3-di-O-tert-butyldimethylsilyl-α-D-arabinofuranoside
  参考文献：
  名称：

  Synthesis of a fluorescent arabinofuranosyl disaccharide: a probe for arabinosyltransferase activity in Mycobacterium tuberculosis

  摘要：

  （5-N,N-二甲基氨基萘-1-磺酰氨基乙基）-5-O-(α-D-阿拉伯糖基)-α-D-阿拉伯糠1被合成作为荧光探针，用于测定结核分枝杆菌中的阿拉伯糖基转移酶活性。版权 © 2001 Elsevier Science Ltd. 保留所有权利。

  DOI：

  10.1016/s0040-4039(00)02161-4
• 作为产物：
  描述：

  tetra-O-acetyl-D-arabinofuranose 在 吡啶 、 咪唑 、 甲醇 、 ammonium hydroxide 、 sodium azide 、 三氟化硼乙醚 、 四氯化锡 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 56.5h， 生成 2-azidoethyl 5-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-2,3-di-O-tert-butyldimethylsilyl-α-D-arabinofuranoside
  参考文献：
  名称：

  Synthesis of a fluorescent arabinofuranosyl disaccharide: a probe for arabinosyltransferase activity in Mycobacterium tuberculosis

  摘要：

  （5-N,N-二甲基氨基萘-1-磺酰氨基乙基）-5-O-(α-D-阿拉伯糖基)-α-D-阿拉伯糠1被合成作为荧光探针，用于测定结核分枝杆菌中的阿拉伯糖基转移酶活性。版权 © 2001 Elsevier Science Ltd. 保留所有权利。

  DOI：

  10.1016/s0040-4039(00)02161-4

文献信息

• Synthesis of a fluorescent arabinofuranosyl disaccharide: a probe for arabinosyltransferase activity in Mycobacterium tuberculosis
  作者：Ashish K Pathak、Vibha Pathak、Namita Bansal、Joseph A Maddry、Robert C Reynolds

  DOI：10.1016/s0040-4039(00)02161-4

  日期：2001.2

  (5-N,N-Dimethylaminonaphthale-1-sulfonamidoethyl)-5-O-(alpha -D-arabinofuranosyl)-alpha -D-arabonofuran 1 was synthesized as a fluorescent probe for the determination of arabinosyltransferase activity in mycobacterium tuberculosis. (C) 2001 Elsevier Science Ltd. All rights reserved.

  （5-N,N-二甲基氨基萘-1-磺酰氨基乙基）-5-O-(α-D-阿拉伯糖基)-α-D-阿拉伯糠1被合成作为荧光探针，用于测定结核分枝杆菌中的阿拉伯糖基转移酶活性。版权 © 2001 Elsevier Science Ltd. 保留所有权利。
• Disaccharide analogs as probes for glycosyltransferases in Mycobacterium tuberculosis
  作者：Ashish K. Pathak、Vibha Pathak、Lainne Seitz、Sudagar S. Gurcha、Gurdyal S. Besra、James M. Riordan、Robert C. Reynolds

  DOI：10.1016/j.bmc.2007.04.012

  日期：2007.8

  Glycosyltransferases (GTs) play a crucial role in mycobacterial cell wall biosynthesis and are necessary for the survival of mycobacteria. Hence, these enzymes are potential new drug targets for the treatment of tuberculosis (TB), especially multiple drug-resistant TB (MDR-TB). Herein, we report the efficient syntheses of Araf(alpha 1 -> 5)Araf, Ga1f(beta 1 -> 5)Galf and Galf(beta 1 -> 6)Galf disaccharides possessing a 5-N,N-dimethylaminonaphthalene-l-sulfonamidoethyl (dansyl) unit that were prepared as fluorescent disaccharide acceptors for arabinosyl- and galactosyl-transferases, respectively. Such analogs may offer advantages relative to radiolabeled acceptors or donors for studying the enzymes and for assay development and compound screening. Additionally, analogs possessing a 5-azidonaphthalene-1-sulfonamidoethyl unit were prepared as photoaffinity probes for then-potential utility in studying active site labeling of the GTs (arabinosyl and galactosyl) in MYcobacterium tuberculosis (MTB). Beyond their preparation, initial biological testing and kinetic analysis of these disaccharides as acceptors toward glycosyltransferases are also presented. (C) 2007 Elsevier Ltd. All rights reserved.