methyl 2-acetamido-2-deoxy-3-O-deoxy-3-O-<(R)-2-propionyl-(L-1-aminomethyl)phosphonic acid>-β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-acetamido-2-deoxy-3-O-deoxy-3-O-<(R)-2-propionyl-(L-1-aminomethyl)phosphonic acid>-β-D-glucopyranoside
• 英文别名: [(1R)-1-[[(2R)-2-[(2R,3S,4R,5R,6R)-5-acetamido-3-hydroxy-2-(hydroxymethyl)-6-methoxyoxan-4-yl]oxypropanoyl]amino]ethyl]phosphonic acid
• 化学式: C₁₄H₂₇N₂O₁₀P
• 分子量: 414.35
• InChiKey: HQLQSGNGGHRQPV-UIBSCBFDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.1
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  184
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  2-acetamido-1,4,6-tri-O-acetyl-2-deoxy-3-O-<(R)-2-propionyl-(L-1-aminoethyl)phosphonic acid dimethyl ester>-α,β-D-glucopyranose 在 lithium hydroxide 、 磷酸 作用下， 生成 [(R)-1-(2-Hydroxy-propionylamino)-ethyl]-phosphonic acid 、 [(R)-1-(2-Hydroxy-propionylamino)-ethyl]-phosphonic acid monomethyl ester 、 methyl 2-acetamido-2-deoxy-3-O-deoxy-3-O-<(R)-2-propionyl-(L-1-aminomethyl)phosphonic acid>-β-D-glucopyranoside 、 2-acetamido-2-deoxy-3-O-<(R)-2-propionyl-(L-1-aminoethyl)phosphonic acid>-β-D-glucopyranosyl phosphate
  参考文献：
  名称：

  Synthesis ofN-acetylmuramic acid derivatives as potential inhibitors of the D-glutamic acid-adding enzyme

  摘要：

  Compounds containing N-acetyl-D-muramic acid and (L-1-aminoethyl)phosphonic acid were designed as potential inhibitors of the D-glutamic acid-adding enzyme of the biosynthesis of bacterial peptidoglycan. 2-Acetamido-2-deoxy-3-O-[(R)-2-propionyl-(L-1-aminoethyl)phosphonic acid]-D-glucopyranose (3) was synthesized. 2-Acetamido-1,4,6-tri-O-acetyl-2-deoxy-3-O-[(R)-2-propionyl- (L-l-aminoethyl) phosphonic acid dimethyl ester]-alpha,beta-D-glucopyranose (9) was also prepared and was submitted to the MacDonald reaction in order to introduce a phosphate group on the anomeric position. A complex mixture of phosphorylated or/and methylated derivatives of 3 was obtained. They were purified by h.p.l.c. and characterized by analyses of hexosamine, amino acid and labile phosphate, and by plasma desorption mass spectrometry. Neither 3 nor its derivatives inhibited the D-glutamic acid-adding enzyme from Escherichia coli.

  DOI：

  10.1002/prac.19953370176