N-carbobenzyloxy-L-phenylalanine 8-aminooctylamide | 915796-93-9

• 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-carbobenzyloxy-L-phenylalanine 8-aminooctylamide
• CAS: 915796-93-9
• 化学式: C₂₅H₃₅N₃O₃
• 分子量: 425.571
• InChiKey: HIYXIGVMISUQPZ-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.94
• 重原子数：
  31.0
• 可旋转键数：
  14.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  93.45
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-carbobenzyloxy-L-phenylalanine 8-aminooctylamide 、 丙烯酰氯 在 三乙胺 作用下， 以 乙腈 为溶剂， 以46%的产率得到benzyl N-[(2S)-1-oxo-3-phenyl-1-[8-(prop-2-enoylamino)octylamino]propan-2-yl]carbamate
  参考文献：
  名称：

  Synthesis and evaluation of peptidic irreversible inhibitors of tissue transglutaminase

  摘要：

  Herein we report the synthesis and the evaluation of eight novel compounds as irreversible inhibitors of transglutaminase (TGase). These compounds are based on a minimal peptidic scaffold shown previously [Chem. Biol. 2005, 12, 469-475] to confer affinity for the TGase active site and bear electrophilic groups such as alpha,beta-un saturated amide, chloroacetamide or maleimide; their general structure being Cbz-Phe-spacer-electrophile. The affinity conferred by the Cbz-Phe scaffold was determined by comparison to N-propylacrylamide and the length of the spacer was also varied to evaluate its importance. The inhibitory efficiencies (k(inact)/K-I) of these compounds vary up to 10(5) M-1 min(-1), among the highest reported for derivatives based on this simple Cbz-Phe peptidic scaffold. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.09.011
• 作为产物：
  描述：

  N-苄氧羰基-L-苯丙氨酸 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 1.83h， 生成 N-carbobenzyloxy-L-phenylalanine 8-aminooctylamide
  参考文献：
  名称：

  Synthesis and evaluation of peptidic irreversible inhibitors of tissue transglutaminase

  摘要：

  Herein we report the synthesis and the evaluation of eight novel compounds as irreversible inhibitors of transglutaminase (TGase). These compounds are based on a minimal peptidic scaffold shown previously [Chem. Biol. 2005, 12, 469-475] to confer affinity for the TGase active site and bear electrophilic groups such as alpha,beta-un saturated amide, chloroacetamide or maleimide; their general structure being Cbz-Phe-spacer-electrophile. The affinity conferred by the Cbz-Phe scaffold was determined by comparison to N-propylacrylamide and the length of the spacer was also varied to evaluate its importance. The inhibitory efficiencies (k(inact)/K-I) of these compounds vary up to 10(5) M-1 min(-1), among the highest reported for derivatives based on this simple Cbz-Phe peptidic scaffold. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.09.011