6-bromo-cytidine | 255723-82-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-bromo-cytidine
• 英文别名: 4-amino-6-bromo-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
• CAS: 255723-82-1
• 化学式: C₉H₁₂BrN₃O₅
• 分子量: 322.115
• InChiKey: VOOUBKYMWRTICK-YXZULKJRSA-N

物化性质

• 沸点：
  555.4±60.0 °C(Predicted)
• 密度：
  2.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  129
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-bromo-cytidine 在 sodium methylate 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
• 作为产物：
  描述：

  胞苷 在 吡啶 、 溴 、 溶剂黄146 作用下， 生成 6-bromo-cytidine
  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

文献信息

• US6020483A
  申请人：——

  公开号：US6020483A

  公开（公告）日：2000-02-01
• US6890736B1
  申请人：——

  公开号：US6890736B1

  公开（公告）日：2005-05-10