6-amino-2-oxo-3-β-D-ribofuranosyl-2,3-dihydro-pyrimidine-4-carboximidic acid methyl ester | 58630-00-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 6-amino-2-oxo-3-β-D-ribofuranosyl-2,3-dihydro-pyrimidine-4-carboximidic acid methyl ester
• 英文别名: 6-amino-2-oxo-3-β-D-ribofuranosyl-2,3-dihydro-pyrimidine-4-carboximidic acid methyl ester；Methyl Cytidin-6-carboximidat
• CAS: 58630-00-5
• 化学式: C₁₁H₁₆N₄O₆
• 分子量: 300.271
• InChiKey: GLEYAARWGULFBS-VPCXQMTMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.59
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  163.91
• 氢给体数：
  5.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  胞苷 在 吡啶 、 溴 、 sodium methylate 、 溶剂黄146 作用下， 以 二甲基亚砜 为溶剂， 生成 6-amino-2-oxo-3-β-D-ribofuranosyl-2,3-dihydro-pyrimidine-4-carboximidic acid methyl ester
  参考文献：
  名称：

  Active Site Probes for Yeast OMP Decarboxylase: Inhibition Constants of UMP and Thio-Substituted UMP Analogues and Greatly Reduced Activity toward CMP-6-Carboxylate

  摘要：

  The catalytic mechanism of orotidine-5'-monophosphate decarboxylase (ODCase, EC 4.1.1.23) involves a proton-sensitive step, probably proton donation to one of the carbonyl oxygens of the substrate, and may also include participation of a Zn2+ ion. To probe the active site for these mechanistic features, thio-substituted analogues of the product UMP were used as inhibitors of yeast ODCase. The intrinsic inhibition constants of the anionic pyrimidines were calculated using the measured inhibition constants and the pK(a) values of the respective compounds. 4-ThioUMP is a stronger inhibitor than UMP, while 2-thioUMP has a K-i virtually the same as that for UMP. A potential alternate substrate, CMP-6-carboxylate, has been synthesized and found to have undetectable activity and weak binding to ODCase. The results are discussed in a unified model for catalysis involving protonation at O2 and a proposed Zn2+ interaction at O4, (C) 1999 Academic Press.

  DOI：

  10.1006/bioo.1999.1140