(2-azido-4,6-di-O-benzyl-2,3-dideoxy-3-fluoro-α-D-glucopyranosyl)-1-dibenzylphosphate | 1334530-12-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2-azido-4,6-di-O-benzyl-2,3-dideoxy-3-fluoro-α-D-glucopyranosyl)-1-dibenzylphosphate
• 英文别名: (2R,3S,4R,5R,6R)-3-azido-4-fluoro-2-[oxido-bis(phenylmethoxy)phosphaniumyl]oxy-5-phenylmethoxy-6-(phenylmethoxymethyl)oxane
• CAS: 1334530-12-9
• 化学式: C₃₄H₃₅FN₃O₇P
• 分子量: 647.64
• InChiKey: AAMYSWWIHUVOSS-SLXQPGMDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  46
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  92.8
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2-azido-4,6-di-O-benzyl-2,3-dideoxy-3-fluoro-α-D-glucopyranosyl)-1-dibenzylphosphate 在 20% palladium hydroxide-activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以90%的产率得到2-Amino-2,3-dideoxy-3-fluoro-α-D-glucopyranosyl-1-phosphate
  参考文献：
  名称：

  Design and synthesis of novel cell wall inhibitors of Mycobacterium tuberculosis GlmM and GlmU

  摘要：

  GlmM and GlmU are key enzymes in the biosynthesis of UDP-N-acetyl-D-glucosamine (UDP-GlcNAc), an essential precursor of peptidoglycan and the rhamnose-GlcNAc linker region in the mycobacterial cell wall. These enzymes are involved in the conversion of two important precursors of UDP-GlcNAc, glucosamine-6-phosphate (GlcN-6-P) and glucosamine-1-phosphate (GlcN-1-P). GlmM converts GlcN-6-P to GlcN-1-P, GlmU is a bifunctional enzyme, whereby GlmU converts GlcN-1-P to GlcNAc-1-P and then catalyzes the formation of UDP-GlcNAc from GlcNAc-1-P and uridine triphosphate. In the present study, methyl 2-amino-2-deoxyl-alpha-D-glucopyranoside 6-phosphate (1 alpha), methyl 2-amino-2deoxyl-beta-D-glucopyranoside 6-phosphate (1 beta), two analogs of GlcN-6-P, were synthesized as GlmM inhibitors; 2-azido-2-deoxy-alpha-D-glucopyranosyl phosphate (2) and 2-amino-2,3-dideoxy-3-fluoro-alpha-Dglucopyranosyl phosphate (3), analogs of GlcN-1-P, were synthesized firstly as GlmU inhibitors. Compounds 1 alpha, 1 beta, 2, and 3 as possible inhibitors of mycobacterial GlmM and GlmU are reported herein. Compound 3 showed promising inhibitory activities against GlmU, whereas 1 beta, 1 beta and 2 were inactive against GlmM and GlmU even at high concentrations. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.05.024
• 作为产物：
  描述：

  焦磷酸四苄酯 、 2-azido-4,6-di-O-benzyl-2,3-dideoxy-3-fluoro-α/β-D-glucopyranose 在 乙基苯 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正庚烷 为溶剂， 反应 3.25h， 以95%的产率得到(2-azido-4,6-di-O-benzyl-2,3-dideoxy-3-fluoro-α-D-glucopyranosyl)-1-dibenzylphosphate
  参考文献：
  名称：

  Design and synthesis of novel cell wall inhibitors of Mycobacterium tuberculosis GlmM and GlmU

  摘要：

  GlmM and GlmU are key enzymes in the biosynthesis of UDP-N-acetyl-D-glucosamine (UDP-GlcNAc), an essential precursor of peptidoglycan and the rhamnose-GlcNAc linker region in the mycobacterial cell wall. These enzymes are involved in the conversion of two important precursors of UDP-GlcNAc, glucosamine-6-phosphate (GlcN-6-P) and glucosamine-1-phosphate (GlcN-1-P). GlmM converts GlcN-6-P to GlcN-1-P, GlmU is a bifunctional enzyme, whereby GlmU converts GlcN-1-P to GlcNAc-1-P and then catalyzes the formation of UDP-GlcNAc from GlcNAc-1-P and uridine triphosphate. In the present study, methyl 2-amino-2-deoxyl-alpha-D-glucopyranoside 6-phosphate (1 alpha), methyl 2-amino-2deoxyl-beta-D-glucopyranoside 6-phosphate (1 beta), two analogs of GlcN-6-P, were synthesized as GlmM inhibitors; 2-azido-2-deoxy-alpha-D-glucopyranosyl phosphate (2) and 2-amino-2,3-dideoxy-3-fluoro-alpha-Dglucopyranosyl phosphate (3), analogs of GlcN-1-P, were synthesized firstly as GlmU inhibitors. Compounds 1 alpha, 1 beta, 2, and 3 as possible inhibitors of mycobacterial GlmM and GlmU are reported herein. Compound 3 showed promising inhibitory activities against GlmU, whereas 1 beta, 1 beta and 2 were inactive against GlmM and GlmU even at high concentrations. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.05.024