benzyl 2-amino-3-(ethylthio)propanoate

• 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-(ethylthio)propanoate
• 英文别名: Benzyl 2-amino-3-ethylsulfanylpropanoate；benzyl 2-amino-3-ethylsulfanylpropanoate
• 化学式: C₁₂H₁₇NO₂S
• 分子量: 239.338
• InChiKey: XFZSWMYNVAHNHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  乙硫醇 、 benzyl (2S)-2-amino-3-methoxycarbonyloxypropanoate 在 2-Me-3-EtO(CH₂)2O-4-CHO-5-(imidazole-4-propanoyl)-pyridine 、 lithium perchlorate 作用下， 以 乙腈 为溶剂， 反应 22.0h， 以80%的产率得到benzyl 2-amino-3-(ethylthio)propanoate
  参考文献：
  名称：

  β-Replacement reaction of serine-O-carbonate derivatives with thiols catalyzed by a pyridoxal model having an ionophore side-chain

  摘要：

  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。

  DOI：

  10.1039/b206061b

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。
• PREPARATION METHOD FOR 2-AMINO-3-SUBSTITUTED MERCAPTOPROPIONATE DERIVATIVE AND USE THEREOF
  申请人：Jiangsu Tasly Diyi Pharmaceutical Co., Ltd.

  公开号：EP3470408A1

  公开（公告）日：2019-04-17

  The present invention relates to a S-substituted-2-amino-3-mercaptopropionate derivative, a preparation method and an application thereof. The S-substituted-2-amino-3-mercaptopropionate derivative in the present invention has a structure of a formula (A). The present invention also includes an application of the S-substituted-2-amino-3-mercaptopropionate derivative serving as a medicine for treating and/or preventing neurodegenerative diseases, particularly Alzheimer's disease.

  本发明涉及一种 S-取代-2-氨基-3-巯基丙酸酯衍生物及其制备方法和应用。 本发明中的 S-取代-2-氨基-3-巯基丙酸酯衍生物具有式（A）的结构。 本发明还包括 S-取代-2-氨基-3-巯基丙酸酯衍生物作为治疗和/或预防神经退行性疾病，特别是阿尔茨海默病的药物的应用。
• 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.