N-ε-benzyloxycarbonyl-N-α-tert-butoxycarbonyl-L-lysinyl-D-alanyl-D-alanine benzyl ester | 18814-54-5

• 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-ε-benzyloxycarbonyl-N-α-tert-butoxycarbonyl-L-lysinyl-D-alanyl-D-alanine benzyl ester
• 英文别名: Boc-L-Lys(Z)-D-Ala-D-Ala-OBn
• CAS: 18814-54-5
• 化学式: C₃₂H₄₄N₄O₈
• 分子量: 612.723
• InChiKey: GEDWXYIWISQYJZ-PLXFJCCSSA-N

物化性质

• 熔点：
  118-120 °C
• 沸点：
  827.5±65.0 °C(Predicted)
• 密度：
  1.175±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.73
• 重原子数：
  44.0
• 可旋转键数：
  15.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  161.16
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  N-ε-benzyloxycarbonyl-N-α-tert-butoxycarbonyl-L-lysinyl-D-alanyl-D-alanine benzyl ester 在 1-羟基苯并三唑 、 三乙胺 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 37.5h， 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-Boc-N'-Cbz-L-赖氨酸 、 D-alanyl-D-alanine benzyl ester trifluoroacetic acid salt 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以32%的产率得到N-ε-benzyloxycarbonyl-N-α-tert-butoxycarbonyl-L-lysinyl-D-alanyl-D-alanine benzyl 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

文献信息

• Synthesis of Peptidoglycan Fragments from<i>Enterococcus faecalis</i>with Fmoc-Strategy for Glycan Elongation
  作者：Ning Wang、Hiroki Hasegawa、Cheng-yuan Huang、Koichi Fukase、Yukari Fujimoto

  DOI：10.1002/asia.201601357

  日期：2017.1.3

  Peptidoglycan (PGN) is an essential structural component of the bacterial cell wall conferring cell shape, which can be recognized by host‐recognition proteins and receptors as well as bacterial surface proteins. In this work, the PGN partial structures from Enterococcus faecalis that contain a tetrasaccharide and an octasaccharide with a unique heptapeptide were synthesized via an Fmoc‐strategy for

  肽聚糖（PGN）是赋予细胞形状的细菌细胞壁的重要结构成分，可以被宿主识别蛋白和受体以及细菌表面蛋白识别。在这项工作中，粪便肠球菌的PGN部分结构是通过Fmoc策略合成的，其中含有四糖和八糖以及独特的七肽，以延长聚糖链。也就是说，在这种有效的合成途径中，使用4'- O -Fmoc保护的二糖作为关键中间体来制备各种PGN片段。具有独特七肽的四糖和八糖都首次成功合成。