2-azidoethyl 2,3,5-O-tri-tert-butyldimethylsilyl-α-D-arabinofuranoside | 488711-88-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-azidoethyl 2,3,5-O-tri-tert-butyldimethylsilyl-α-D-arabinofuranoside
• 英文别名: [(2R,3R,4S,5S)-5-(2-azidoethoxy)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]oxolan-2-yl]methoxy-tert-butyl-dimethylsilane
• CAS: 488711-88-2
• 化学式: C₂₅H₅₅N₃O₅Si₃
• 分子量: 561.985
• InChiKey: JGUHTLBXOOIRMO-CZYKHXBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.84
• 重原子数：
  36
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-azidoethyl 2,3,5-O-tri-tert-butyldimethylsilyl-α-D-arabinofuranoside 在 N-甲基咪唑 、 palladium on activated charcoal 、 N-碘代丁二酰亚胺 、 tin(II) trifluoromethanesulfonate 、 氨 、 甲酸铵 、 四乙基氟化铵水合物 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 2-(5-azidonaphthalene-1-sulfonamido)ethyl 5-O-(α-D-arabinofuranosyl)-α-D-arabinofuranoside
  参考文献：
  名称：

  Synthesis of an arabinofuranosyl disaccharide photoaffinity probe for arabinosyltransferase activity in Mycobacterium tuberculosis

  摘要：

  (5-叠氮萘-1-磺酰氨基乙基)-5-O-(α-L-阿拉伯呋喃核糖基)-α-D-阿拉伯呋喃核苷糖1被合成作为光亲和探针，用于测定阿拉伯糖基转移酶的活性，并用于鉴定在结核分枝杆菌中结合和功能位点。(C)2002 Elsevier Science Ltd. 保留所有权利。

  DOI：

  10.1016/s0960-894x(02)00536-x
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 、 2-ethylazido-α-D-arabinofuranoside 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以90%的产率得到2-azidoethyl 2,3,5-O-tri-tert-butyldimethylsilyl-α-D-arabinofuranoside
  参考文献：
  名称：

  Synthesis of an arabinofuranosyl disaccharide photoaffinity probe for arabinosyltransferase activity in Mycobacterium tuberculosis

  摘要：

  (5-叠氮萘-1-磺酰氨基乙基)-5-O-(α-L-阿拉伯呋喃核糖基)-α-D-阿拉伯呋喃核苷糖1被合成作为光亲和探针，用于测定阿拉伯糖基转移酶的活性，并用于鉴定在结核分枝杆菌中结合和功能位点。(C)2002 Elsevier Science Ltd. 保留所有权利。

  DOI：

  10.1016/s0960-894x(02)00536-x

文献信息

• 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.
• Synthesis of an arabinofuranosyl disaccharide photoaffinity probe for arabinosyltransferase activity in Mycobacterium tuberculosis
  作者：Ashish K. Pathak、Vibha Pathak、Sudagar S. Gurcha、Gurdyal S. Besra、Robert C. Reynolds

  DOI：10.1016/s0960-894x(02)00536-x

  日期：2002.10

  (5-Azidonaphthalene-1-sulfonamidoethyl)- 5-O-(alpha-arabinofuranosyl)-alpha-D-arabino furano side 1 was synthesized as a photoaffinity probe for the determination of arabinosyl transferase activity and for the identification of binding and functional sites in Mycobacterium tuberculosis. (C) 2002 Elsevier Science Ltd. All rights reserved.

  (5-叠氮萘-1-磺酰氨基乙基)-5-O-(α-L-阿拉伯呋喃核糖基)-α-D-阿拉伯呋喃核苷糖1被合成作为光亲和探针，用于测定阿拉伯糖基转移酶的活性，并用于鉴定在结核分枝杆菌中结合和功能位点。(C)2002 Elsevier Science Ltd. 保留所有权利。