methyl 2-amino-2-deoxyl-β-D-glucopyranoside-6-phosphate | 78082-64-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-amino-2-deoxyl-β-D-glucopyranoside-6-phosphate
• 英文别名: methyl 2-amino-2-deoxy-β-D-glucoside 6-phosphate；methyl glucosamine-6-phosphate；[(2R,3S,4R,5R,6R)-5-amino-3,4-dihydroxy-6-methoxyoxan-2-yl]methyl dihydrogen phosphate
• CAS: 78082-64-1
• 化学式: C₇H₁₆NO₈P
• 分子量: 273.18
• InChiKey: ZKRHWMOZEAPULC-NYMZXIIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  152
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  methyl 2-azido-2-deoxy-D-glucopyranoside 在 吡啶 、 platinum(IV) oxide 、 palladium 10% on activated carbon 、 氢气 作用下， 反应 66.0h， 生成 methyl 2-amino-2-deoxyl-β-D-glucopyranoside-6-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

文献信息

• GLMS RIBOSWITCHES, STRUCTURE-BASED COMPOUND DESIGN WITH GLMS RIBOSWITCHES, AND METHODS AND COMPOSITIONS FOR USE OF AND WITH GLMS RIBOSWITCHES
  申请人：Breaker Ronald R.

  公开号：US20100324123A1

  公开（公告）日：2010-12-23

  The glmS riboswitch is a target for antibiotics and other small molecule therapies. Compounds can be used to stimulate, active, inhibit and/or inactivate the glmS riboswitch. The atomic structures of the glmS riboswitch can be used to design new compounds to stimulate, active, inhibit and/or inactivate riboswitches.

  glmS核酸开关是抗生素和其他小分子治疗的靶点。化合物可以用于刺激、激活、抑制和/或失活glmS核酸开关。glmS核酸开关的原子结构可用于设计新的化合物，以刺激、激活、抑制和/或失活核酸开关。
• Methyl 2-amino-2-deoxy-d-glucoside 6-phosphates
  作者：Naohito Ohno、Satoru Yui、Toshiro Yadomae、Toshio Miyazaki

  DOI：10.1016/s0008-6215(00)85933-9

  日期：1981.4