α-2-amino-2,6-dideoxy-D-glucopyranose-6-sulphonic acid | 102803-97-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-2-amino-2,6-dideoxy-D-glucopyranose-6-sulphonic acid
• 英文别名: 2-amino-2,6-dideoxy-6-sulfo-D-glucopyranose；2-amino-2,6-dideoxy-6-sulfo-α-D-glucopyranose；α-D-glucosamine-6-sulfonate；[(2S,3S,4R,5R,6S)-5-amino-3,4,6-trihydroxyoxan-2-yl]methanesulfonic acid
• CAS: 102803-97-4
• 化学式: C₆H₁₃NO₇S
• 分子量: 243.238
• InChiKey: MVXBKKVRCXUSLH-UKFBFLRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  159
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  benzyl 2-deoxy-2-(N-acetylamino)-D-glucopyranoside 在 吡啶 、 盐酸 、 四溴化碳 、 三苯基膦 、 sodium sulfite 作用下， 以 水 为溶剂， 反应 10.75h， 生成 α-2-amino-2,6-dideoxy-D-glucopyranose-6-sulphonic acid 、 β-2-amino-2,6-dideoxy-D-glucopyranose-6-sulphonic acid
  参考文献：
  名称：

  6-磺基-6-脱氧-D-葡萄糖胺及其衍生物的合成和抑菌活性。

  摘要：

  已经合成并合成了6-磺基6-脱氧-D-氨基葡萄糖（GlcN6S），6-磺基6-脱氧-D-氨基葡萄糖（ADGS）及其N-乙酰基和甲酯衍生物作为酶催化的细菌和酵母中的UDP-GlcNAc途径。微摩尔浓度的GlcN6S和ADGS抑制了微生物来源的6-磷酸氨基葡萄糖（GlcN6P）合酶。前者也抑制真菌GlcN6P N-乙酰基转移酶，但浓度为毫摩尔浓度。两种化合物及其N-乙酰基衍生物均具有体外抗菌活性，MIC范围为0.125-2.0 mg mL-1。D-葡糖胺增强了GlcN6S的抗菌活性，但未增强其抗真菌活性，并且观察到ADGP和二肽Nva-FMDP的组合具有协同抗菌作用。

  DOI：

  10.1016/j.carres.2017.06.002

文献信息

• Synthesis and evaluation of an N-acetylglucosamine biosynthesis inhibitor
  作者：Juliana L. Sacoman、Rawle I. Hollingsworth

  DOI：10.1016/j.carres.2011.07.004

  日期：2011.10

  The structural rationale, synthesis and evaluation of an inhibitor designed to block glucosamine synthesis by competitively inhibiting the action of glutamine: fructose-6-phosphate amidotransferase and subsequently reducing the transformation of any glucosamine-6-phosphate formed to UDP-N-acetylglucosamine are described. The inhibitor 2-acetamido-2,6-dideoxy-6-sulfo-D-glucose (D-glucosamine-6-sulfonate) is an analog of glucosamine-6-phosphate in which the phosphate group in the latter is replaced with a sulfonic acid group. The inhibitor is designed to function by three different modes which together reduce UDP-N-acetylglucosamine synthesis. This reduction was confirmed by evaluating the effect of the inhibitor on bacterial cell-wall synthesis and by demonstrating that it inhibits acetylation of glucosamine-6-phosphate competitively and by acting as a surrogate substrate. Inhibition of glucosamine production or suitably activated glucosamine in bacteria leads to disruption of the peptidoglycan structure, which results in softening, bulging, deformation, fragility and lysis of the cells. These modifications were documented by scanning electron microscopy for bacteria treated with the inhibitor. They were observed for inhibitor concentrations in the 20 mg/mL range for Escherichia coli and Bacillus subtilis and the 5 mg/mL range for Rhizobium (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis and antimicrobial activity of 6-sulfo-6-deoxy-D-glucosamine and its derivatives
  作者：Kornelia Skarbek、Iwona Gabriel、Piotr Szweda、Marek Wojciechowski、Muna A. Khan、Boris Görke、Sławomir Milewski、Maria J. Milewska

  DOI：10.1016/j.carres.2017.06.002

  日期：2017.8

  inhibitory towards fungal GlcN6P N-acetyl transferase, but at millimolar concentrations. Both compounds and their N-acetyl derivatives exhibited antimicrobial in vitro activity, with MICs in the 0.125-2.0 mg mL-1 range. Antibacterial but not antifungal activity of GlcN6S was potentiated by D-glucosamine and a synergistic antibacterial effect was observed for combination of ADGP and a dipeptide Nva-FMDP

  已经合成并合成了6-磺基6-脱氧-D-氨基葡萄糖（GlcN6S），6-磺基6-脱氧-D-氨基葡萄糖（ADGS）及其N-乙酰基和甲酯衍生物作为酶催化的细菌和酵母中的UDP-GlcNAc途径。微摩尔浓度的GlcN6S和ADGS抑制了微生物来源的6-磷酸氨基葡萄糖（GlcN6P）合酶。前者也抑制真菌GlcN6P N-乙酰基转移酶，但浓度为毫摩尔浓度。两种化合物及其N-乙酰基衍生物均具有体外抗菌活性，MIC范围为0.125-2.0 mg mL-1。D-葡糖胺增强了GlcN6S的抗菌活性，但未增强其抗真菌活性，并且观察到ADGP和二肽Nva-FMDP的组合具有协同抗菌作用。