N_α-carbobenzyloxy-L-2-amino-3-(oxiranecarbonylamino)propionic acid | 366781-04-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N_α-carbobenzyloxy-L-2-amino-3-(oxiranecarbonylamino)propionic acid
• CAS: 366781-04-6
• 化学式: C₁₄H₁₆N₂O₆
• 分子量: 308.291
• InChiKey: SUGDIYICIIAIRY-VUWPPUDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.12
• 重原子数：
  22.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  117.26
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  半胱胺盐酸盐 、 N_α-carbobenzyloxy-L-2-amino-3-(oxiranecarbonylamino)propionic acid 以 水 、 丙酮 为溶剂， 反应 12.0h， 以100%的产率得到N_α-carbobenzyloxy-L-2-amino-3-(2-hydroxy-3-(2-aminoethylthio)propionylamino)propionic acid
  参考文献：
  名称：

  Evaluation of novel dipeptide-bound α,β-unsaturated amides and epoxides as irreversible inhibitors of guinea pig liver transglutaminase

  摘要：

  Herein, we report the results of irreversible inhibition of guinea pig liver transglutaminase (TGase) by a series of 24 novel dipeptides containing either an alpha,beta -unsaturated amide or an epoxide functional group. Their inactivation rate constants were measured using a direct continuous spectrophotometric method and were found to vary between 421x10(3) and 3000 x 10(3) M-1 min(-1). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00101-8
• 作为产物：
  描述：

  3-氨基-N-Cbz-L-丙氨酸 在 二甲基二环氧乙烷 、 三乙胺 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 12.0h， 生成 N_α-carbobenzyloxy-L-2-amino-3-(oxiranecarbonylamino)propionic acid
  参考文献：
  名称：

  Synthesis of dipeptide-bound epoxides and α,β-unsaturated amides as potential irreversible transglutaminase inhibitors

  摘要：

  Herein we report the synthesis of 24 novel peptides Lis potential irreversible inactivators of transglutaminase (TGase). These peptides were designed to resemble Cbz-L-Gln-Gly, known to be a good TGase substrate, and to include either alpha,beta -unsaturated amide groups or the corresponding epoxide groups. The side chain length: of the amino acid residue bearing the inhibitor group was also varied in order to permit investigation of this effect. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00292-9