Cbz-ΔGlu-OH | 96658-31-0

• 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: Cbz-ΔGlu-OH
• 英文别名: 2-{[(Benzyloxy)carbonyl]amino}pent-2-enedioic acid；2-(phenylmethoxycarbonylamino)pent-2-enedioic acid
• CAS: 96658-31-0
• 化学式: C₁₃H₁₃NO₆
• 分子量: 279.249
• InChiKey: ZDEKDZYJZIJMMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  Cbz-ΔGlu-OMe 在 McIlvaine buffer 、 2-巯基乙醇 、 papain 作用下， 反应 24.0h， 生成 Cbz-ΔGlu-OH
  参考文献：
  名称：

  木瓜蛋白酶对α-脱氢谷氨酸二甲酯的α-酯的选择性酶水解

  摘要：

  发现 N-苄氧羰基-α-脱氢谷氨酸二甲酯 [Cbz-ΔGlu (OMe)-OMe] 与木瓜蛋白酶在 pH 8.0 的选择性酯水解很容易实现，几乎只得到 Cbz-ΔGlu(OMe)-OH数量上。

  DOI：

  10.1246/cl.1988.2001

文献信息

• Novel and Selective Enzymatic Hydrolysis of γ-Ester of Dimethyl α-Dehydroglutamate with α-Chymotrypsin A
  作者：Chung-gi Shin、Masashi Seki、Nobuyuki Takahashi

  DOI：10.1246/cl.1990.2089

  日期：1990.11

  Selective enzymatic hydrolysis of γ-ester of Cbz–ΔGlu (OMe)–OMe with α-chymotrypsin at pH 9 was readily achieved to give the corresponding α-half ester (Cbz–ΔGlu–OMe) along with a small amount of Cbz–ΔGlu(OMe)–OH and Cbz–ΔGlu–OH.

  Cbz-ΔGlu (OMe)-OMe 的 γ-酯在 pH 9 下用 α-胰凝乳蛋白酶选择性酶水解得到相应的 α-半酯 (Cbz-ΔGlu-OMe) 和少量 Cbz-ΔGlu (OMe)-OH 和 Cbz-ΔGlu-OH。
• Very Selective Enzymatic Hydrolysis of α-Ester of Dimethyl α-Dehydroglutamate with Papain
  作者：Chung-gi Shin、Nobuyuki Takahashi、Yasuchika Yonezawa

  DOI：10.1246/cl.1988.2001

  日期：1988.12.5

  It was found that the selective ester hydrolysis of N-benzyloxycarbonyl-α-dehydroglutamic acid dimethyl ester [Cbz-ΔGlu (OMe)-OMe] with papain at pH 8.0 was achieved readily to give only a Cbz-ΔGlu(OMe)-OH almost quantitatively.

  发现 N-苄氧羰基-α-脱氢谷氨酸二甲酯 [Cbz-ΔGlu (OMe)-OMe] 与木瓜蛋白酶在 pH 8.0 的选择性酯水解很容易实现，几乎只得到 Cbz-ΔGlu(OMe)-OH数量上。
• Dehydrooligopeptides. XIII. Selective Enzymatic Hydrolysis of<i>N</i>-Protected α-Dehydroglutamic Acid Diesters and Their Analogs Using Papain as Catalyst
  作者：Chung-gi Shin、Nobuyuki Takahashi、Masashi Seki

  DOI：10.1246/bcsj.64.3575

  日期：1991.12

  Since the α-ester of α,γ-dimethyl N-benzyloxycarbonyl-α-dehydroglutamate (ΔGlu) was found to be hydrolyzed using papain, a variety of N-protected α-dehydroglutamates and their analogs, both esters of which were the same or different from each other, were newly synthesized and subjected to a similar hydrolysis. Although the substrates, with bulkier ester group at the γ- as well as α-positions, were found to become difficult to hydrolyze, the kind and size of the N-protecting group did not effect the hydrolysis. Moreover, it was found that the length of side chain of the substrate greatly influenced hydrolysis. The present study suggests that papain may become a useful tool for the hydrolysis and coupling of ΔGlu with α-amino acid or peptide.

  由于发现α,γ-二甲基 N-苄氧羰基-α-脱氢谷氨酸（ΔGlu）的α-酯可被木瓜蛋白酶水解，因此新合成了多种 N-保护的α-脱氢谷氨酸及其类似物，这些酯之间存在相同或不同之处，并进行了类似的水解。虽然在 γ 和 α 位上有较多酯基的底物变得难以水解，但 N 保护基的种类和大小并不影响水解。此外，研究还发现底物侧链的长度对水解有很大影响。本研究表明，木瓜蛋白酶可能会成为ΔGlu与α-氨基酸或肽水解和偶联的有用工具。