methyl N-(tert-butoxycarbonyl)-O-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl)-L-serinate | 1241902-83-9

• 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: methyl N-(tert-butoxycarbonyl)-O-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl)-L-serinate
• CAS: 1241902-83-9
• 化学式: C₁₈H₃₄BNO₇
• 分子量: 387.281
• InChiKey: DFUQXRPAKQBDRC-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.55
• 重原子数：
  27.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  92.32
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl N-(tert-butoxycarbonyl)-O-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl)-L-serinate 在 甲醇 、 水 、 potassium carbonate 作用下， 生成
  参考文献：
  名称：

  Probe molecule equipped with boronic acid moiety as a reversible cross-linking group improves its binding affinity

  摘要：

  Syntheses of biotinylated probe molecules of L-glutathione (GSH) equipped with boronic acid moiety and evaluation of their binding affinities against glutathione-S-transferase (GST) were described. It revealed that the presence of boronic acid moiety in an appropriate position enhances binding affinity of GSH probe toward GST probably by forming a reversible cross-link. Among prepared, the boronate-containing probe 8b exhibited the highest recovering ability of GST from Escherichia coli cell lysate. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.05.052
• 作为产物：
  描述：

  频那醇硼烷 、 (S)-O-allyl-N-Boc-serine methyl ester 在 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 1,2-双(二苯基膦)乙烷 作用下， 以 二氯甲烷 为溶剂， 以76%的产率得到methyl N-(tert-butoxycarbonyl)-O-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl)-L-serinate
  参考文献：
  名称：

  Probe molecule equipped with boronic acid moiety as a reversible cross-linking group improves its binding affinity

  摘要：

  Syntheses of biotinylated probe molecules of L-glutathione (GSH) equipped with boronic acid moiety and evaluation of their binding affinities against glutathione-S-transferase (GST) were described. It revealed that the presence of boronic acid moiety in an appropriate position enhances binding affinity of GSH probe toward GST probably by forming a reversible cross-link. Among prepared, the boronate-containing probe 8b exhibited the highest recovering ability of GST from Escherichia coli cell lysate. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.05.052