2-azidoethyl 2,3-di-O-(p-methoxybenzyl)-β-D-galactofuranoside | 946847-13-8

• 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-di-O-(p-methoxybenzyl)-β-D-galactofuranoside
• CAS: 946847-13-8
• 化学式: C₂₄H₃₁N₃O₈
• 分子量: 489.525
• InChiKey: WQTNASSSUWXRLV-OYTPZHDJSA-N

反应信息

• 作为反应物：
  描述：

  2-azidoethyl 2,3-di-O-(p-methoxybenzyl)-β-D-galactofuranoside 、 4-甲氧基氯苄 在 二正丁基氧化锡 、 cesium fluoride 作用下， 以 甲苯 、 N,N-二甲基甲酰胺 为溶剂， 以90%的产率得到2-azidoethyl 2,3,6-tri-O-(p-methoxybenzyl)-β-D-galactofuranoside
  参考文献：
  名称：

  Disaccharide analogs as probes for glycosyltransferases in Mycobacterium tuberculosis

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2007.04.012
• 作为产物：
  描述：

  2-azidoethyl 5,6-O-isopropylidene-2,3-di-O-(p-methoxybenzyl)-β-D-galactofuranoside 在 水 、 溶剂黄146 作用下， 反应 4.0h， 以77%的产率得到2-azidoethyl 2,3-di-O-(p-methoxybenzyl)-β-D-galactofuranoside
  参考文献：
  名称：

  Disaccharide analogs as probes for glycosyltransferases in Mycobacterium tuberculosis

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2007.04.012