Cbz-Glu(OAll)-OH | 1188524-00-6

• 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: Cbz-Glu(OAll)-OH
• 英文别名: (2S)-5-oxo-2-(phenylmethoxycarbonylamino)-5-prop-2-enoxypentanoic acid
• CAS: 1188524-00-6
• 化学式: C₁₆H₁₉NO₆
• 分子量: 321.33
• InChiKey: ZVMOTXDUDRTJOT-ZDUSSCGKSA-N

物化性质

• 沸点：
  525.2±50.0 °C(Predicted)
• 密度：
  1.235±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  23
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  L-glutamic acid diallyl ester 在 Alcalase-cross-linked-enzyme-aggregates 作用下， 以 叔丁醇 为溶剂， 反应 16.0h， 以85%的产率得到Cbz-Glu(OAll)-OH
  参考文献：
  名称：

  A versatile and selective chemo-enzymatic synthesis of β-protected aspartic and γ-protected glutamic acid derivatives

  摘要：

  Two versatile, high yielding, and efficient chemo-enzymatic methods for the synthesis of beta-protected Asp and gamma-protected Glu derivatives using Alcalase are described. The first method is based on the alpha-selective enzymatic hydrolysis of symmetrical aspartyl and glutamyl diesters. The second method involving mixed diesters comprises a three-step protocol using (i) alpha-selective enzymatic methyl-esterification, (ii) chemical beta-esterification, and finally (iii) alpha-selective enzymatic methyl ester hydrolysis. The yields of the purified beta- and gamma-esters range from 77% to 91%. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.03.130

文献信息

• <i>Bacillus subtilis</i>Esterase (BS2) and its Double Mutant Have Different Selectivity in the Removal of Carboxyl Protecting Groups
  作者：Efrosini Barbayianni、Christoforos G. Kokotos、Sebastian Bartsch、Christina Drakou、Uwe T. Bornscheuer、George Kokotos

  DOI：10.1002/adsc.200900325

  日期：2009.10

  An esterase from Bacillus subtilis (BS2) and its double mutant E188W/M193C quickly hydrolyze n-butyl, n-propyl, methoxyethyl and allyl esters. The wild-type BS2 preferentially removes such esters from the γ-position of glutamate diesters, while the engineered enzyme has a reversed selectivity removing esters from the α-position of glutamate diesters. Automated docking and molecular dynamic simulations

  从酯酶枯草芽孢杆菌（BS2）和它的双突变体E188W / M193C迅速水解Ñ丁基，Ñ丙基，甲氧基乙基和烯丙基酯。野生型BS2优先从谷氨酸二酯的γ-位除去这些酯，而工程酶具有相反的选择性，从谷氨酸二酯的α-位除去酯。进行了自动对接和分子动力学模拟，以了解不同区域选择性的分子原因。