Carbonylbis-l-valine | 930574-07-5

• 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: Carbonylbis-l-valine
• 英文别名: (2S)-2-[[(1S)-1-carboxy-2-methylpropyl]carbamoylamino]-3-methylbutanoic acid
• CAS: 930574-07-5
• 化学式: C₁₁H₂₀N₂O₅
• 分子量: 260.29
• InChiKey: HAQWTQZRCQINBZ-YUMQZZPRSA-N

物化性质

• 沸点：
  521.5±35.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N,N'-2-[di-(benzylisopentanoate)]-urea 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 以65 mg的产率得到Carbonylbis-l-valine
  参考文献：
  名称：

  SylC Catalyzes Ureido-Bond Formation During Biosynthesis of the Proteasome Inhibitor Syringolin A

  摘要：

  Syringolins are a class of cyclic tripeptide natural products that are potent and irreversible inhibitors of the eukaryotic proteasome. In addition to being hybrid NRPS/PKS molecules, they also feature an unusual ureido-linkage (red) between two amino acid monomers. Here we report the first in vitro characterization of enzymatic ureido-linkage formation which is catalyzed by an NRPS, SylC. Using C-13- and O-18-labeling studies, we show that biosynthesis occurs via N-carboxylation to form an initial N-carboxy-aminoacyl-S-Ppant enzyme intermediate which undergoes intramolecular cyclization followed by condensation with a second amino acid to form the ureido-containing dipeptide product.

  DOI：

  10.1021/ja909170u