H2N-(S)-Ala-(2R,4S)-4-chloro-boroPro-OH | 1395229-80-7

• 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: H2N-(S)-Ala-(2R,4S)-4-chloro-boroPro-OH
• 英文别名: [(2R,4S)-1-[(2S)-2-aminopropanoyl]-4-chloropyrrolidin-2-yl]boronic acid
• CAS: 1395229-80-7
• 化学式: C₇H₁₄BClN₂O₃
• 分子量: 220.464
• InChiKey: HPESIFUOBXUHNB-ZLUOBGJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.45
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  86.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  tert-butyl N-[(2S)-1-[(2R,4R)-4-hydroxy-2-[(1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.02,6]decan-4-yl]pyrrolidin-1-yl]-1-oxopropan-2-yl]carbamate 在 四氯化碳 、 三氯化硼 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 H2N-(S)-Ala-(2R,4S)-4-chloro-boroPro-OH
  参考文献：
  名称：

  4-Substituted boro-proline dipeptides: Synthesis, characterization, and dipeptidyl peptidase IV, 8, and 9 activities

  摘要：

  The boroProline-based dipeptidyl boronic acids were among the first DPP-IV inhibitors identified, and remain the most potent known. We introduced various substitutions at the 4-position of the boroProline ring regioselectively and stereoselectively, and incorporated these aminoboronic acids into a series of 4-substituted boroPro-based dipeptides. Among these dipeptidyl boronic acids, Arg-(4S)-boroHyp (4q) was the most potent inhibitor of DPP-IV, DPP8 and DPP9, while (4S)-Hyp-(4R)-boroHyp (4o) exhibited the most selectivity for DPP-IV over DPP8 and DPP9. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.07.033

文献信息

• 4-Substituted boro-proline dipeptides: Synthesis, characterization, and dipeptidyl peptidase IV, 8, and 9 activities
  作者：Wengen Wu、Yuxin Liu、Lawrence J. Milo、Ying Shu、Peng Zhao、Youhua Li、Iwona Woznica、Gengli Yu、David G. Sanford、Yuhong Zhou、Sarah E. Poplawski、Beth A. Connolly、James L. Sudmeier、William W. Bachovchin、Jack H. Lai

  DOI：10.1016/j.bmcl.2012.07.033

  日期：2012.9

  The boroProline-based dipeptidyl boronic acids were among the first DPP-IV inhibitors identified, and remain the most potent known. We introduced various substitutions at the 4-position of the boroProline ring regioselectively and stereoselectively, and incorporated these aminoboronic acids into a series of 4-substituted boroPro-based dipeptides. Among these dipeptidyl boronic acids, Arg-(4S)-boroHyp (4q) was the most potent inhibitor of DPP-IV, DPP8 and DPP9, while (4S)-Hyp-(4R)-boroHyp (4o) exhibited the most selectivity for DPP-IV over DPP8 and DPP9. (C) 2012 Elsevier Ltd. All rights reserved.