N-tert-butoxycarbonyl-L-alanyl-D-glutamic acid α-benzyl-γ-p-nitrophenyl ester | 678159-24-5

• 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: N-tert-butoxycarbonyl-L-alanyl-D-glutamic acid α-benzyl-γ-p-nitrophenyl ester
• 英文别名: Boc-L-Ala-D-Glu-α-OBn-γ-ONp
• CAS: 678159-24-5
• 化学式: C₂₆H₃₁N₃O₉
• 分子量: 529.547
• InChiKey: CNMOMLXYGCNEKF-LAUBAEHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.42
• 重原子数：
  38.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  163.17
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  N-tert-butoxycarbonyl-L-alanyl-D-glutamic acid α-benzyl-γ-p-nitrophenyl ester 在 1-羟基苯并三唑 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.5h， 生成 L-alanyl-D-glutaminyl-(α-benzyl)-γ-N-ε-benzyloxycarbonyl-L-lysinyl-D-alanyl-D-alanine benzyl ester trifluoroacetic acid salt
  参考文献：
  名称：

  Synthesis of a Fragment of Bacterial Cell Wall

  摘要：

  Cell wall is indispensable for survival of bacteria. This large molecular "mesh" encases the entire cytoplasm of bacteria, and it is comprised of repeating backbone units of N-acetyl-glucosamine (NAG)-N-acetyl-muramic acid (NAM). A pentapeptide is attached to each of the lactyl units of the N-acetyl-muramic acid. The cell wall has both cross-linked and non-cross-linked components. In the present paper, we have devised a synthetic route for the preparation of a fragment of the cell wall comprised of a tetrasaccharide (NAG-NAM-NAG-NAM), along with the two appended peptides. We also report the syntheses of three glycosyl donors (compounds 5, 7, and 9) and three glycosyl acceptors (compounds 4, 6, and 8) based on the D-glucosamine structure as a building unit. The synthetic strategy that is disclosed is generally useful in construction of other natural products containing the D-glucosamine as a building block.

  DOI：

  10.1021/jo035583k
• 作为产物：
  描述：

  N-叔丁氧羰基-L-丙氨酸 4-硝基苯酯 在 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 N-tert-butoxycarbonyl-L-alanyl-D-glutamic acid α-benzyl-γ-p-nitrophenyl ester
  参考文献：
  名称：

  Synthesis of a Fragment of Bacterial Cell Wall

  摘要：

  Cell wall is indispensable for survival of bacteria. This large molecular "mesh" encases the entire cytoplasm of bacteria, and it is comprised of repeating backbone units of N-acetyl-glucosamine (NAG)-N-acetyl-muramic acid (NAM). A pentapeptide is attached to each of the lactyl units of the N-acetyl-muramic acid. The cell wall has both cross-linked and non-cross-linked components. In the present paper, we have devised a synthetic route for the preparation of a fragment of the cell wall comprised of a tetrasaccharide (NAG-NAM-NAG-NAM), along with the two appended peptides. We also report the syntheses of three glycosyl donors (compounds 5, 7, and 9) and three glycosyl acceptors (compounds 4, 6, and 8) based on the D-glucosamine structure as a building unit. The synthetic strategy that is disclosed is generally useful in construction of other natural products containing the D-glucosamine as a building block.

  DOI：

  10.1021/jo035583k