D,L-N-Carbamoyl-homocysteinthiolacton | 38869-97-5

• 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: D,L-N-Carbamoyl-homocysteinthiolacton
• 英文别名: N-carbamylhomocysteine thiolactone；α-Ureido-γ-thiolbutyrolacton；(2-oxo-tetrahydro-thiophen-3-yl)-urea；(2-Oxothiolan-3-yl)urea；(2-oxothiolan-3-yl)urea
• CAS: 38869-97-5
• 化学式: C₅H₈N₂O₂S
• 分子量: 160.197
• InChiKey: WMKPPSUSMBMETA-UHFFFAOYSA-N

物化性质

• 沸点：
  361.2±42.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  97.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  D,L-N-Carbamoyl-homocysteinthiolacton 在 盐酸 作用下， 反应 2.0h， 以85.8%的产率得到D,L-5-(2'-Mercaptoethyl)-hydantoin
  参考文献：
  名称：

  Chemoenzymatische Synthese von N6-Carbamoyl-D-4-thialysin und N7-Carbamoyl-D-homo-5-thialysin

  摘要：

  The combination of classical chemical and enzymatical methods opens a way to highly functionalized chiral molecules like N6-carbamoyl-D-4-thialysine (5) or N7-carbamoyl-D-homo-5-thialysine (6). The biotransformation of the corresponding hydantoines with Agrobacterium radiobacter is creating the desired D chirality.

  DOI：

  10.1002/prac.19923340303
• 作为产物：
  描述：

  D,L-4,5-Dihydro-3-isocyanato-(3H)-thiophen-2-on 在 氨 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以73.8%的产率得到D,L-N-Carbamoyl-homocysteinthiolacton
  参考文献：
  名称：

  Chemoenzymatische Synthese von N6-Carbamoyl-D-4-thialysin und N7-Carbamoyl-D-homo-5-thialysin

  摘要：

  The combination of classical chemical and enzymatical methods opens a way to highly functionalized chiral molecules like N6-carbamoyl-D-4-thialysine (5) or N7-carbamoyl-D-homo-5-thialysine (6). The biotransformation of the corresponding hydantoines with Agrobacterium radiobacter is creating the desired D chirality.

  DOI：

  10.1002/prac.19923340303

文献信息

• Analogs of carbamyl aspartate as inhibitors of dihydroorotase: preparation of boronic acid transition-state analogs and a zinc chelator carbamylhomocysteine
  作者：David H. Kinder、Sandra K. Frank、Matthew M. Ames

  DOI：10.1021/jm00164a055

  日期：1990.2

  carboxylic acid esters focused on a Curtius rearrangement as a key step following a malonic ester synthesis. This was followed by carbamoylation of the free amine under nonaqueous neutral conditions with Si(NCO)4. The ethyl ester was a competitive inhibitor of DHO with an apparent Ki of 5.07 microM, while the nonesterified analogue and the methyl ester were not effective inhibitors. None of the compounds were

  二氢乳清酶（DHO）在从头嘧啶生物合成途径中催化氨基甲酰天冬氨酸（CA）转化为二氢乳清酸酯（DO）。很少有有效的DHO抑制剂被报道，因此，作为一种抗肿瘤药物的开发策略，对该反应的阻断尚未广泛地进行。利用两种基于机制的策略，我们设计并制备了潜在的CA DHO抑制剂类似物。一种策略是用硼酸代替CA的γ-羧基部分。该取代产生形成稳定的带电荷的四面体中间体并模拟酶-底物过渡态的化合物。CA及其羧酸酯的硼酸类似物的制备侧重于Curtius重排，这是丙二酸酯合成之后的关键步骤。随后在非水中性条件下用Si（NCO）4对游离胺进行氨基甲酰化。乙酯是DHO的竞争性抑制剂，表观Ki为5.07 microM，而非酯化类似物和甲酯不是有效的抑制剂。没有一种化合物对培养的L1210细胞具有细胞毒性。还制备了活性部位导向的含巯基的锌螯合剂。该类似物不可逆地抑制了该酶，但在L1210生长抑制中也无效。还制备了活性部位导
• Chemoenzymatische Synthese von N6-Carbamoyl-D-4-thialysin und N7-Carbamoyl-D-homo-5-thialysin
  作者：Karlheinz Drauz、Matthias Kottenhahn、Herbert Klenk

  DOI：10.1002/prac.19923340303

  日期：——

  The combination of classical chemical and enzymatical methods opens a way to highly functionalized chiral molecules like N6-carbamoyl-D-4-thialysine (5) or N7-carbamoyl-D-homo-5-thialysine (6). The biotransformation of the corresponding hydantoines with Agrobacterium radiobacter is creating the desired D chirality.