6-methoxycarbonyl uridine | 55878-70-1

• 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-methoxycarbonyl uridine
• 英文别名: orotidine methyl ester；6-Methoxycarbonyluridin；Orotidinmethylester；2,6-dioxo-3-β-D-ribofuranosyl-1,2,3,4-tetrahydro-pyrimidine-4-carboxylic acid methyl ester；methyl 3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,6-dioxopyrimidine-4-carboxylate
• CAS: 55878-70-1
• 化学式: C₁₁H₁₄N₂O₈
• 分子量: 302.241
• InChiKey: OJUKBVCCFZIKKF-ZOQUXTDFSA-N

物化性质

• 密度：
  1.666±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  146
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  6-methoxycarbonyl uridine 在 水 、 sodium hydroxide 作用下， 以 乙腈 为溶剂， 以100%的产率得到乳清苷
  参考文献：
  名称：

  通过分子内核苷合成牛尿苷。

  摘要：

  分子内核苷化方法可轻松轻松获得高产的牛膝苷。值得注意的是，乳清酸酯本身被用作异头位置的离去基团。该方法具有容易获得具有治疗意义的酪蛋白衍生物的潜力，这涉及益生元形成核苷。

  DOI：

  10.1039/c5cc00111k
• 作为产物：
  描述：

  尿嘧啶核苷 在 硫酸 咪唑 、 水 、 三氟乙酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 6-methoxycarbonyl uridine
  参考文献：
  名称：

  WO2008/83465

  摘要：

  公开号：

文献信息

• Orotidine‐Containing RNA: Implications for the Hierarchical Selection (Systems Chemistry Emergence) of RNA
  作者：Eun‐Kyong Kim、Vincent Martin、Ramanarayanan Krishnamurthy

  DOI：10.1002/chem.201702912

  日期：2017.9.12

  orotidine itself is absent in RNA. Given the prebiotic and biological relevance of orotic acid vis‐à‐vis uracil, we investigated orotidine‐containing RNA oligonucleotides and show that they have severely compromised base‐pairing properties. While not unexpected, these results suggest that the emergence of extant RNA cannot just be a consequence of the plausible prebiotic formation of its chemical constituents/building

  HCN的标准生物碱基的益生元合成是RNA世界假说的基石。然而，它们在RNA原始途径中的作用仍存在争议。从HCN开始的完全相同的过程也产生了乳清酸，该乳清酸（通过Orotidine）在现有生物学中从头合成尿苷和胞苷（RNA中的信息碱基对）起着至关重要的作用。但是，RNA中不存在奥洛替丁本身。鉴于乳清酸相对于尿嘧啶的益生元和生物学相关性，我们研究了含奥洛替丁的RNA寡核苷酸，并表明它们具有严重损害的碱基配对特性。尽管并不出乎意料，但这些结果表明，现存RNA的出现不能仅仅是其化学成分/结构单元似宜的益生元形成的结果。
• ODCASE INHIBITORS FOR THE TREATMENT OF MALARIA
  申请人：Kotra Lakshmi P.

  公开号：US20090221524A1

  公开（公告）日：2009-09-03

  The present invention includes methods of treating or preventing malaria by administering an anti-malarial effective amount of 6-substituted uridine derivatives to a subject need thereof. The invention also includes new 6-substituted uridine derivatives for use as therapeutics, in particular to treat malaria.

  本发明涉及通过向需要治疗或预防疟疾的受体施用抗疟疾有效量的6-取代尿嘧啶衍生物来治疗或预防疟疾的方法。本发明还包括新的6-取代尿嘧啶衍生物，用于作为治疗剂，特别是用于治疗疟疾。
• Pyrimidine Derivatives As Anticancer Agents
  申请人：Kotra Lakshmi P.

  公开号：US20100056468A1

  公开（公告）日：2010-03-04

  The present invention includes methods of treating or preventing cancer by administering an effective amount of 6-substituted pyrimidine derivatives of the Formula I to a subject need thereof:

  本发明涉及通过向需要该治疗的受体施用公式I的6-取代嘧啶衍生物的有效量来治疗或预防癌症的方法：
• Substrate Distortion Contributes to the Catalysis of Orotidine 5′-Monophosphate Decarboxylase
  作者：Masahiro Fujihashi、Toyokazu Ishida、Shingo Kuroda、Lakshmi P. Kotra、Emil F. Pai、Kunio Miki

  DOI：10.1021/ja408197k

  日期：2013.11.20

  Orotidine 5'-monophosphate decarboxylase (OD-Case) accelerates the decarboxylation of orotidine 5'-monophosphate (OMP) to uridine 5'-monophosphate (UMP) by 17 orders of magnitude. Eight new crystal structures with ligand analogues combined with computational analyses of the enzyme's short-lived intermediates and the intrinsic electronic energies to distort the substrate and other ligands improve our understanding of the still controversially discussed reaction mechanism. In their respective complexes, 6-methyl-UMP displays significant distortion of its methyl substituent bond, 6-amino-UMP shows the competition between the K72 and C6 substituents for a position close to D70, and the methyl and ethyl esters of OMP both induce rotation of the carboxylate group substituent out of the plane of the pyrimidine ring. Molecular dynamics and quantum mechanics/molecular mechanics computations of the enzyme-substrate complex also show the bond between the carboxylate group and the pyrimidine ring to be distorted, with the distortion contributing a 10-15% decrease of the Delta Delta G(double dagger) value. These results are consistent with ODCase using both substrate distortion and transition-state stabilization, primarily exerted by K72, in its catalysis of the OMP decarboxylation reaction.
• WO2007/38859
  申请人：——

  公开号：——

  公开（公告）日：——