benzyl 2-amino-3-(benzylthio)propanoate | 39801-36-0

• 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: benzyl 2-amino-3-(benzylthio)propanoate
• 英文别名: S-benzyl-DL-cysteine benzyl ester；S-Benzyl-DL-cystein-benzylester；Benzyl 2-amino-3-benzylsulfanylpropanoate
• CAS: 39801-36-0
• 化学式: C₁₇H₁₉NO₂S
• 分子量: 301.409
• InChiKey: RWISUDSSXJFKIY-UHFFFAOYSA-N

物化性质

• 沸点：
  446.1±45.0 °C(Predicted)
• 密度：
  1.186±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  77.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 生成 benzyl 2-amino-3-(benzylthio)propanoate
  参考文献：
  名称：

  Maclaren et al., Australian Journal of Chemistry, 1958, vol. 11, p. 345,355

  摘要：

  DOI：

文献信息

• Artificial model for cystathionine β-synthase: construction of a catalytic cycle with a pyridoxal model compound having an ionophore function
  作者：Kazuyuki Miyashita、Hidenobu Murafuji、Hiroshi Iwaki、Eito Yoshioka、Takeshi Imanishi

  DOI：10.1016/s0040-4020(03)00665-3

  日期：2003.6

  Catalytic transformation of serine-O-carbonate to S-aryl cysteine derivatives was successfully achieved in the presence of Li+ by the use of a pyridoxal model compound having an ionophore function, which is the first example mimicking cystathionine β-synthase, artificially.

  在Li +存在下，通过使用具有离子载体功能的吡ido醛模型化合物，成功地将丝氨酸-O-碳酸酯催化转化为S-芳基半胱氨酸衍生物，这是人工模拟胱硫醚β-合酶的第一个实例。
• β-Replacement reaction of serine-O-carbonate derivatives with thiols catalyzed by a pyridoxal model having an ionophore side-chain
  作者：Kazuyuki Miyashita、Hidenobu Murafuji、Hiroshi Iwaki、Eito Yoshioka、Takeshi Imanishi

  DOI：10.1039/b206061b

  日期：——

  Serine-O-carbonate derivatives, including peptides having a serine-O-carbonate residue at the N-terminal position, are catalytically transformed into S-substituted cysteine derivatives employing the pyridoxal model having an ionophore function in the presence of Li+; this is the first artificial model mimicking cystathionine β-synthase.

  丝氨酸-O-碳酸酯衍生物，包括在 N 端位置具有丝氨酸-O-碳酸酯残基的肽，在 Li+ 的存在下，利用具有离子发酵功能的吡哆醛模型，催化转化为 S-取代的半胱氨酸衍生物；这是第一个模拟胱硫醚合成酶的人工模型。
• Artificial model for cystathionine β-synthase: efficient β-replacement reaction with thiols employing a novel pyridoxal model compound having an imidazole function
  作者：Kazuyuki Miyashita、Hidenobu Murafuji、Hiroshi Iwaki、Eito Yoshioka、Takeshi Imanishi

  DOI：10.1016/s0040-4020(03)00666-5

  日期：2003.6

  As a second-generation pyridoxal model compound for cystathionine beta-synthase, we designed a novel model compound having an ionophore function and an imidazole function, application of which to the beta-replacement reaction with various thiols smoothly took place to give S-substituted cysteines. Peptides having a serine-O-carbonate residue at the N-terminal position were also converted to the corresponding peptides having an S-substituted cysteine residue under the catalytic conditions of the novel pyridoxal model compound. (C) 2003 Elsevier Science Ltd. All rights reserved.