Boc-Ser-Ala-OBzl | 74257-91-3

• 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: Boc-Ser-Ala-OBzl
• 英文别名: benzyl (2S)-2-[[(2S)-3-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]propanoate
• CAS: 74257-91-3
• 化学式: C₁₈H₂₆N₂O₆
• 分子量: 366.414
• InChiKey: DWLJTTZAWDGBNE-JSGCOSHPSA-N

物化性质

• 沸点：
  562.2±50.0 °C(Predicted)
• 密度：
  1.192±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Boc-Ser-Ala-OBzl 在 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.5h， 生成 PhO-CH2CO-Ser-Ala-OBzl
  参考文献：
  名称：

  Synthesis of Analogs of D-Ala--D-Ala as Potential Inhibitors of Bacterial Cell Wall Biosynthesis.

  摘要：

  The syntheses of the L,L- and D,D-stereoisomers of N- phenoxyacetyl -X-alanine in which X = Ser, Ala( beta Cl ) or Arg, are described. The antibacterial activity of these peptides and some of their synthetic intermediates has been examined. Four of the intermediates in which X = Ala( beta Cl ) and Arg(NO2), which possess C-terminal benzyl ester groups, were active against viridans streptococci and Streptococcus agalactiae. The D,D-enantiomers were more active than the corresponding L,L-isomers. None of the compounds were active against beta-lactamase producing bacteria or acted as beta-lactamase inhibitors.

  DOI：

  10.3891/acta.chem.scand.38b-0005
• 作为产物：
  描述：

  BOC-L-丝氨酸 、 L-丙氨酸苄酯对甲苯磺酸盐 在 N-乙基吗啉 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以63%的产率得到Boc-Ser-Ala-OBzl
  参考文献：
  名称：

  Synthesis of Analogs of D-Ala--D-Ala as Potential Inhibitors of Bacterial Cell Wall Biosynthesis.

  摘要：

  The syntheses of the L,L- and D,D-stereoisomers of N- phenoxyacetyl -X-alanine in which X = Ser, Ala( beta Cl ) or Arg, are described. The antibacterial activity of these peptides and some of their synthetic intermediates has been examined. Four of the intermediates in which X = Ala( beta Cl ) and Arg(NO2), which possess C-terminal benzyl ester groups, were active against viridans streptococci and Streptococcus agalactiae. The D,D-enantiomers were more active than the corresponding L,L-isomers. None of the compounds were active against beta-lactamase producing bacteria or acted as beta-lactamase inhibitors.

  DOI：

  10.3891/acta.chem.scand.38b-0005

文献信息

• Efficient Synthesis of S-Linked Glycopeptides in Aqueous Solution by a Convergent Strategy
  作者：Xiangming Zhu、Richard R. Schmidt

  DOI：10.1002/chem.200305163

  日期：2004.2.20

  In naturally occurring glycopeptides and glycoproteins the glycan residues generally possess N- and O-linkages to the peptide backbone. Here we report the synthesis of the corresponding S-linked glycopeptides by a convergent strategy to provide compounds which should be quite stable to glycosidases. To this end, peptides that contain beta-bromoalanine and gamma-bromohomoalanine were generated either

  在天然存在的糖肽和糖蛋白中，聚糖残基通常具有与肽主链的N-和O-键。在这里，我们报告了通过收敛策略合成相应的S-连接糖肽，以提供对糖苷酶应相当稳定的化合物。为此，分别通过丝氨酸和高丝氨酸残基的溴化或通过相应氨基酸的标准连接直接产生含有β-溴丙氨酸和γ-溴高丙氨酸的肽。通过已知方法制备了O-乙酰基保护的GalNAc，GlcNAc和乳糖的1-硫代糖。在含有TBAHS和NaHCO（3）的乙酸乙酯/水两相系统中，或在由DMF /水组成且含有NaHCO（3）的单相系统中，硫糖与这些肽的反应，可以干净，几乎定量地得到所需的S-连接糖肽。该反应对于O-未保护的1-硫代糖也很好地起作用。