Pr-L-Ala-N3 | 1027093-02-2

• 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: Pr-L-Ala-N3
• 英文别名: (2S)-2-(propanoylamino)propanoyl azide
• CAS: 1027093-02-2
• 化学式: C₆H₁₀N₄O₂
• 分子量: 170.171
• InChiKey: IRTUHNAWRFCQDB-BYPYZUCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  60.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Pr-L-Ala-N3 在 盐酸 、 sodium hydroxide 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 吡啶 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 169.5h， 生成 Pr-L-Ala-ambo-buthionine sulfoximine phosphate
  参考文献：
  名称：

  Synthesis of new peptide inhibitors of the meso-diaminopimelate-adding enzyme

  摘要：

  In order to obtain inhibitors of the meso-diaminopimelate-adding enzyme, which catalyzes an early reaction in the biosynthesis of bacterial peptidoglycan, several new peptide derivatives of general formula N(alpha)-propionyl-L-alanyl-D(or ambo)-Xaa were synthesized: four transition-state analogs (Xaa = phosphinothricin, homocysteic acid, buthionine sulfoximine, buthionine sulfoximine phosphate), three analogS of gamma-D-glutamyl phosphate (Xaa = 3-phosphonoacetamido-alanine, 3-phosphonomethylamino-aspartic acid, 2-amino-6-phosphonohexanoic acid), and one derivative with Xaa = ornithine. After preincubation with partially purified meso-diaminopimelate-adding enzyme from Escherichia coli, peptide derivatives with Xaa = buthionine sulfoximine, 3-phosphonoacetamido-alanine and 2-amino-6-phosphonohexanoic acid appeared to be among the best inhibitors obtained up to date, with I50 values between 0.6 and 1.2 mM. When the two first compounds wert tested for in vitro antibacterial activity, they gave negative results.

  DOI：

  10.1016/0223-5234(92)90021-r
• 作为产物：
  描述：

  Pr-L-Ala-NHNH2 在 盐酸 、 sodium nitrite 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 Pr-L-Ala-N3
  参考文献：
  名称：

  Synthesis of new peptide inhibitors of the meso-diaminopimelate-adding enzyme

  摘要：

  In order to obtain inhibitors of the meso-diaminopimelate-adding enzyme, which catalyzes an early reaction in the biosynthesis of bacterial peptidoglycan, several new peptide derivatives of general formula N(alpha)-propionyl-L-alanyl-D(or ambo)-Xaa were synthesized: four transition-state analogs (Xaa = phosphinothricin, homocysteic acid, buthionine sulfoximine, buthionine sulfoximine phosphate), three analogS of gamma-D-glutamyl phosphate (Xaa = 3-phosphonoacetamido-alanine, 3-phosphonomethylamino-aspartic acid, 2-amino-6-phosphonohexanoic acid), and one derivative with Xaa = ornithine. After preincubation with partially purified meso-diaminopimelate-adding enzyme from Escherichia coli, peptide derivatives with Xaa = buthionine sulfoximine, 3-phosphonoacetamido-alanine and 2-amino-6-phosphonohexanoic acid appeared to be among the best inhibitors obtained up to date, with I50 values between 0.6 and 1.2 mM. When the two first compounds wert tested for in vitro antibacterial activity, they gave negative results.

  DOI：

  10.1016/0223-5234(92)90021-r

文献信息

• Synthesis of new peptide inhibitors of the meso-diaminopimelate-adding enzyme
  作者：P Le Roux、G Auger、J van Heijenoort、D Blanot

  DOI：10.1016/0223-5234(92)90021-r

  日期：1992.12

  In order to obtain inhibitors of the meso-diaminopimelate-adding enzyme, which catalyzes an early reaction in the biosynthesis of bacterial peptidoglycan, several new peptide derivatives of general formula N(alpha)-propionyl-L-alanyl-D(or ambo)-Xaa were synthesized: four transition-state analogs (Xaa = phosphinothricin, homocysteic acid, buthionine sulfoximine, buthionine sulfoximine phosphate), three analogS of gamma-D-glutamyl phosphate (Xaa = 3-phosphonoacetamido-alanine, 3-phosphonomethylamino-aspartic acid, 2-amino-6-phosphonohexanoic acid), and one derivative with Xaa = ornithine. After preincubation with partially purified meso-diaminopimelate-adding enzyme from Escherichia coli, peptide derivatives with Xaa = buthionine sulfoximine, 3-phosphonoacetamido-alanine and 2-amino-6-phosphonohexanoic acid appeared to be among the best inhibitors obtained up to date, with I50 values between 0.6 and 1.2 mM. When the two first compounds wert tested for in vitro antibacterial activity, they gave negative results.