2-acetamido-1,6-anhydro-2-deoxy-4-O-p-methoxybenzyl-3-O-{(2R)-propionyl-[L-alanine-p-nitroanilide]-2-yl}-β-D-glucopyranose | 1257316-87-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-acetamido-1,6-anhydro-2-deoxy-4-O-p-methoxybenzyl-3-O-{(2R)-propionyl-[L-alanine-p-nitroanilide]-2-yl}-β-D-glucopyranose
• CAS: 1257316-87-2
• 化学式: C₂₈H₃₄N₄O₁₀
• 分子量: 586.599
• InChiKey: FRZSKUGLTNQRKR-KOWCPIKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.67
• 重原子数：
  42.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  176.59
• 氢给体数：
  3.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  2-acetamido-1,6-anhydro-2-deoxy-4-O-p-methoxybenzyl-3-O-{(2R)-propionyl-[L-alanine-p-nitroanilide]-2-yl}-β-D-glucopyranose 在 水 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以10%的产率得到2-acetamido-1,6-anhydro-2-deoxy-3-O-{(2R)-propionyl-[L-alanine-p-nitroanilide]-2-yl}-β-D-glucopyranose
  参考文献：
  名称：

  1,6-AnhMurNAc derivatives for assay development of amidase AmiD

  摘要：

  Various peptidoglycan fragments were synthesized from two anhydro-muramic acid derivatives protected with a Bn or a PMB group at the 4th position, in homogenate phase or on a solid support. In order to facilitate HPLC detection, a chromophoric group was attached to the peptide chain. The periplasmic amidase sAmiD of Escherichia coli was used to cleave the amide bond between the lactyl group of the MurNAc and the alpha-amino group of L-Ala where the peptide chain was at least a dipeptide (L-Ala-gamma-D-Glu) amidated by benzylamine on the c-carboxyl group of D-Glu. In the presence of a tripeptide chain (L-Ala-gamma-D-Glu-L-Lys) or a tetrapeptide chain (L-Ala-gamma-D-Glu-m-A(2)pm-D-Ala) higher hydrolysis rates were observed. We have also demonstrated that the presence of TNB on the epsilon-amino group of L-Lys only has a small influence on the hydrolysis capacity of sAmiD. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.09.010
• 作为产物：
  描述：

  (R)-2-(((1R,2S,3R,4R,5R)-4-acetamido-2-((4-methoxybenzyl)oxy)-6,8-dioxabicyclo[3.2.1]octan-3-yl)oxy)propanoic acid 、 L-丙氨酰对硝基苯胺盐酸盐 在 N-甲基吗啉 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 49.0h， 以73%的产率得到2-acetamido-1,6-anhydro-2-deoxy-4-O-p-methoxybenzyl-3-O-{(2R)-propionyl-[L-alanine-p-nitroanilide]-2-yl}-β-D-glucopyranose
  参考文献：
  名称：

  1,6-AnhMurNAc derivatives for assay development of amidase AmiD

  摘要：

  Various peptidoglycan fragments were synthesized from two anhydro-muramic acid derivatives protected with a Bn or a PMB group at the 4th position, in homogenate phase or on a solid support. In order to facilitate HPLC detection, a chromophoric group was attached to the peptide chain. The periplasmic amidase sAmiD of Escherichia coli was used to cleave the amide bond between the lactyl group of the MurNAc and the alpha-amino group of L-Ala where the peptide chain was at least a dipeptide (L-Ala-gamma-D-Glu) amidated by benzylamine on the c-carboxyl group of D-Glu. In the presence of a tripeptide chain (L-Ala-gamma-D-Glu-L-Lys) or a tetrapeptide chain (L-Ala-gamma-D-Glu-m-A(2)pm-D-Ala) higher hydrolysis rates were observed. We have also demonstrated that the presence of TNB on the epsilon-amino group of L-Lys only has a small influence on the hydrolysis capacity of sAmiD. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.09.010