uridine 5'-[bis(trioctylammonium)phosphate] | 62540-53-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷酸
• 英文名称: uridine 5'-[bis(trioctylammonium)phosphate]
• CAS: 62540-53-8
• 化学式: C₉H₁₃N₂O₉P*C₂₄H₅₁N
• 分子量: 677.86
• InChiKey: CEQNXRKNFFAWSU-DYIFJOFMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.64
• 重原子数：
  46.0
• 可旋转键数：
  25.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  174.55
• 氢给体数：
  5.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  uridine 5'-[bis(trioctylammonium)phosphate] 在 无机焦磷酸酶 、 uridine-5'-diphosphoglucose pyrophosphorylase 、 sodium perchlorate 、 三丁基焦磷酸铵 作用下， 以 乙腈 为溶剂， 反应 24.0h， 生成 尿苷(5')二氢二磷酰(1)-alpha-D-葡萄糖
  参考文献：
  名称：

  Convenient syntheses of cytidine 5'-triphosphate, guanosine 5'-triphosphate, and uridine 5'-triphosphate and their use in the preparation of UDP-glucose, UDP-glucuronic acid, and GDP-mannose

  摘要：

  DOI：

  10.1021/jo00293a030
• 作为产物：
  描述：

  三辛胺 、 尿苷5-单磷酸 以 甲醇 、 乙醇 为溶剂， 反应 1.0h， 生成 uridine 5'-[bis(trioctylammonium)phosphate]
  参考文献：
  名称：

  Convenient syntheses of cytidine 5'-triphosphate, guanosine 5'-triphosphate, and uridine 5'-triphosphate and their use in the preparation of UDP-glucose, UDP-glucuronic acid, and GDP-mannose

  摘要：

  DOI：

  10.1021/jo00293a030

文献信息

• Chemoenzymatic synthesis of thio-nod factor intermediates — Enzymatic transfer of glucosamine on thiochitobiose derivatives
  作者：Latino Loureiro Morais、Hideya Yuasa、Khalil Bennis、Isabelle Ripoche、France-Isabelle Auzanneau

  DOI：10.1139/v06-043

  日期：2006.4.1

  The chemoenzymatic syntheses of thioanalogues of nodulation factors in which the nonreducing end glucosamine residue is available for the introduction of the fatty acid moiety at the free NH₂group are reported. We are describing the chemical synthesis of UDP-GlcNH₂and its use in the enzymatic transfer of GlcNH₂by the bovine galactosyltransferase (EC 2.4.1.90) onto O-4 of the nonreducing end N-acetylglucosamine residues of chitobiose, thiochitobiose, and allyl thiochitobioside. The enzymatic reactions on chitobiose and thiochitobiose were followed by TLC and MALDI MS and showed about 50% conversion of the disaccharides to the desired products. However, these reducing trisaccharides could not be obtained totally free of salts and degraded on ion exchange chromatography. Thus, we investigated the enzymatic transfer on the nonreducing allyl thiochitobioside analogue. We describe here the chemical synthesis of this thiodisaccharide and the enzymatic transfer of GlcNH₂at O-4 of its nonreducing end glucosamine residue to give the desired allyl thiotrisaccharide. This thiotrisaccharide was obtained pure in 41% yield and was characterized by¹H NMR (HSQC) and HRMS.Key words: nodulation factors, synthesis, enzymatic transfer, thiooligosaccharides, UDP-glucosamine.

  本研究报道了用化学酶法合成结瘤因子硫代类似物的过程，在这些类似物中，非还原端葡糖胺残基可用于在游离 NH2 基上引入脂肪酸分子。我们介绍了 UDP-GlcNH2 的化学合成及其在牛半乳糖基转移酶（EC 2.4.1.90）将 GlcNH2 酶促转移到壳寡糖、硫代壳寡糖和烯丙基硫代壳寡糖的非还原端 N-乙酰葡糖胺残基的 O-4 上的应用。利用 TLC 和 MALDI MS 对壳寡糖和硫代壳寡糖的酶促反应进行了跟踪，结果表明这些二糖约有 50% 转化为所需产物。然而，这些还原性三糖不能完全不含盐分，并在离子交换色谱中降解。因此，我们研究了非还原性烯丙基硫代几丁质类似物的酶促转移。我们在此描述了这种硫代二糖的化学合成及其非还原端氨基葡萄糖残基 O-4 上 GlcNH2 的酶促转移，从而得到所需的烯丙基硫代三糖。这种硫代异糖的纯度为 41%，并通过 1H NMR (HSQC) 和 HRMS 进行了表征。
• Noort, D.; Marel, G. A. van der; Gen, A. van der, Recueil des Travaux Chimiques des Pays-Bas, 1991, vol. 110, # 2, p. 53 - 56
  作者：Noort, D.、Marel, G. A. van der、Gen, A. van der、Mulder, G. J.、Boom, J. H. van

  DOI：——

  日期：——
• Synthesis and structure–activity relationship of uracil nucleotide derivatives towards the identification of human P2Y 6 receptor antagonists
  作者：Diana Meltzer、Ophir Ethan、Guillaume Arguin、Yael Nadel、Ortal Danino、Joanna Lecka、Jean Sévigny、Fernand-Pierre Gendron、Bilha Fischer

  DOI：10.1016/j.bmc.2015.07.004

  日期：2015.9

  P2Y(6) receptor (P2Y(6)-R) is involved in various physiological and pathophysiological events. With a view to set rules for the design of UDP-based reversible P2Y(6)-R antagonists as potential drugs, we established structure-activity relationship of UDP analogues, bearing modifications at the uracil ring, ribose moiety, and the phosphate chain. For instance, C5-phenyl- or 3-NMe-uridine-5'-alpha,beta-methylene-diphosphonate, 16 and 23, or lack of 2'-OH, in 12-15, resulted in loss of both agonist and antagonist activity toward hP2Y(6)-R. However, uridylyl phosphosulfate, 19, selectively inhibited hP2Y(6)-R (IC50 112 mu M) versus P2Y(2)/(4)-Rs. In summary, we have established a comprehensive SAR for hP2Y(6)-R ligands towards the development of hP2Y(6)-R antagonists. (C) 2015 Elsevier Ltd. All rights reserved.