(2-chloro-4-nitrophenyl) 6'-deoxy-6'-methoxyamino-β-D-glucopyranoside | 1397274-82-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-chloro-4-nitrophenyl) 6'-deoxy-6'-methoxyamino-β-D-glucopyranoside
• 英文别名: (2S,3R,4S,5S,6R)-2-(2-chloro-4-nitrophenoxy)-6-[(methoxyamino)methyl]oxane-3,4,5-triol
• CAS: 1397274-82-6
• 化学式: C₁₃H₁₇ClN₂O₈
• 分子量: 364.74
• InChiKey: MBZONFCICSTCTE-UJPOAAIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  146
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2-chloro-4-nitrophenyl) 6'-deoxy-6'-methoxyamino-β-D-glucopyranoside 、 尿苷-5’-二磷酸 在 OleD variant TDP-16 (P₆₇T/S₃₁₂F/A₂₄₂L/Q₂₆₈V) 作用下， 以 二甲基亚砜 为溶剂， 反应 30.0h， 以88%的产率得到UDP-6-deoxy-6-methoxyamino-β-D-glucopyranoside
  参考文献：
  名称：

  Natural Product Disaccharide Engineering through Tandem Glycosyltransferase Catalysis Reversibility and Neoglycosylation

  摘要：

  A two-step strategy for disaccharide modulation using vancomycin as a model is reported. The strategy relies upon a glycosyltransferase-catalyzed 'reverse' reaction to enable the facile attachment of an alkoxyamine-bearing sugar to the vancomycin core. Neoglycosylation of the corresponding aglycon led to a novel set of vancomycin 1,6-disaccharide variants. While the in vitro antibacterial properties of corresponding vancomycin 1,6-disaccharide analogs were equipotent to the parent antibiotic, the chemoenzymatic method presented is expected to be broadly applicable.

  DOI：

  10.1021/ol3023374
• 作为产物：
  描述：

  2-氯-4-硝基苯酚 在 吡啶 、 咪唑 、 甲醇 、 四丁基溴化铵 、 sodium methylate 、 sodium cyanoborohydride 、 戴斯-马丁氧化剂 、 溶剂黄146 、 乙酰氯 、 sodium hydroxide 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 155.0h， 生成 (2-chloro-4-nitrophenyl) 6'-deoxy-6'-methoxyamino-β-D-glucopyranoside
  参考文献：
  名称：

  Natural Product Disaccharide Engineering through Tandem Glycosyltransferase Catalysis Reversibility and Neoglycosylation

  摘要：

  A two-step strategy for disaccharide modulation using vancomycin as a model is reported. The strategy relies upon a glycosyltransferase-catalyzed 'reverse' reaction to enable the facile attachment of an alkoxyamine-bearing sugar to the vancomycin core. Neoglycosylation of the corresponding aglycon led to a novel set of vancomycin 1,6-disaccharide variants. While the in vitro antibacterial properties of corresponding vancomycin 1,6-disaccharide analogs were equipotent to the parent antibiotic, the chemoenzymatic method presented is expected to be broadly applicable.

  DOI：

  10.1021/ol3023374