UMP

• 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: UMP
• 英文别名: [(2S,3R,4S,5S)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
• 化学式: C₉H₁₃N₂O₉P
• 分子量: 324.184
• InChiKey: DJJCXFVJDGTHFX-PSQAKQOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  166
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  UMP 在 mono tributylammonium pyrophosphate 、 N,N'-二环己基碳二亚胺 作用下， 以 吡啶 、 水 、 叔丁醇 为溶剂， 反应 66.0h， 生成 P¹,P⁴-di(L-uridine 5'-)tetraphosphate tetrasodium salt
  参考文献：
  名称：

  First synthesis of enantio-uracil dinucleotide, comparison of physicochemical properties of their enantiomers, and separation by chiral column chromatography

  摘要：

  Enantio-uracil dinucleotide 5, which consists Of two L-uridylic acids and one pyrophosphate, was synthesized for the first time in our laboratory. Benzolyated L-uridine was prepared by a stereoselective glycosylation of silylated uracil with L-1-O-acetyl-2,3,5-tri-O-benzoylribose (L-ABR 7). After deprotection, L-uridine 9 was converted to P-1,P-4-di(L-uridine 5'-) tetraphosphate tetrasodium salt (L-UP4U 5) by treatment of L-UMP morpholidate 10c with triethylammonium pyrophosphate (TEA-PPi 11b). Spectral data of synthesized L-Up(4)U 5 are given in the references. All spectral data were identical with those of UP4U 3 except the specific rotation, which showed a positive value compared to UP,U 3 having a negative value. Furthermore, the separation by chiral column chromatography was investigated. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.09.142
• 作为产物：
  描述：

  2',3',5'-tri-O-benzoyl-L-uridine 在 磷酸三乙酯 、 sodium methylate 、 三氯氧磷 作用下， 以 甲醇 为溶剂， 反应 23.0h， 生成 UMP
  参考文献：
  名称：

  First synthesis of enantio-uracil dinucleotide, comparison of physicochemical properties of their enantiomers, and separation by chiral column chromatography

  摘要：

  Enantio-uracil dinucleotide 5, which consists Of two L-uridylic acids and one pyrophosphate, was synthesized for the first time in our laboratory. Benzolyated L-uridine was prepared by a stereoselective glycosylation of silylated uracil with L-1-O-acetyl-2,3,5-tri-O-benzoylribose (L-ABR 7). After deprotection, L-uridine 9 was converted to P-1,P-4-di(L-uridine 5'-) tetraphosphate tetrasodium salt (L-UP4U 5) by treatment of L-UMP morpholidate 10c with triethylammonium pyrophosphate (TEA-PPi 11b). Spectral data of synthesized L-Up(4)U 5 are given in the references. All spectral data were identical with those of UP4U 3 except the specific rotation, which showed a positive value compared to UP,U 3 having a negative value. Furthermore, the separation by chiral column chromatography was investigated. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.09.142
• 作为试剂：
  描述：

  glucose 1-phosphate 、 α-倒捻子素 在 glycosyltransferase 、 乙酰磷酸 、 5’-三磷酸腺苷 、 UMP 、 magnesium chloride 作用下， 反应 2.0h， 生成 α-mangostin 3,6-di-O-β-D-glucopyranoside 、 α-mangostin 3-O-β-D-glucopyranoside 、 α-mangostin 6-O-β-D-glucopyranoside
  参考文献：
  名称：

  YjiC对α-芒果苷单糖苷产物特异性的突变分析

  摘要：

  糖基转移酶 (GT) 是药物开发过程中次级代谢产物后修饰的关键酶。在我们之前的研究中，一锅酶系统使用野生型糖基转移酶 (YjiC) 但 α-芒果素 3-O 以更高的比例生产了 α-芒果苷 3,6-di-O-β-D-吡喃葡萄糖苷 (Mg1) -β-D-吡喃葡萄糖苷 (Mg2) 表现出明显更高的抗菌活性。本研究侧重于地衣芽孢杆菌起源的柔性糖基转移酶，通过诱变来检查参与糖基化的活性位点残基，以确定对 Mg2 的产品特异性。YjiC 产生的 H298A、H298S 和 H298C 突变体对糖基化产物 (Mg2) 表现出区域特异性，是本研究的目标。Mg1的生产格局下降到63（H298A），与野生型 YjiC 相比，85 (H298S) 和 95% (H298C) 的产量。尿苷 5'-二磷酸 (UDP) 的增加导致酶活性的抑制和整个系统中尿苷 5'-二磷酸葡萄糖 (UDP-葡萄糖) 的产生对于特定的糖

  DOI：

  10.1016/j.enzmictec.2018.08.001

文献信息

• A Nucleotide Dimer Synthesis Without Protecting Groups Using Montmorillonite as Catalyst
  作者：Prakash C. Joshi、Michael F. Aldersley、Dmitri V. Zagorevskii、James P. Ferris

  DOI：10.1080/15257770.2012.701787

  日期：2012.7

  including heterochiral and chimeric syntheses. This greener chemistry has enabled the synthesis of dimers from activated nucleotides themselves, activated nucleotides with nucleosides, and activated nucleotides with nucleotide 5′-monophosphates. [Supplemental materials are available for this article. Go to the publisher's online edition of Nucleosides, Nucleotides & Nucleic Acids to view the free supplemental

  已经开发了提供包含天然或非天然核苷残基的核苷酸二聚体的合成。在不存在保护基的情况下，将核糖核苷5'-磷酰胺基咪唑化物添加到吸附在蒙脱石上的核苷中性pH下。大约30％的咪唑化物被转化为2'-5'二聚体和3'-5'二聚体，其余的则被水解为5'-单磷酸酯。通过多种组合进行的实验表明，该方法可能会受到限制，包括杂手性和嵌合合成。这种绿色化学方法使得能够从活化的核苷酸本身，具有核苷的活化核苷酸和具有核苷酸5'-单磷酸酯的活化核苷酸合成二聚体。 [本文提供补充材料。转到发布者的在线版《核苷酸，核苷酸和核酸》以查看免费的补充文件。]
• Progress in demonstrating total homochiral selection in montmorillonite-catalyzed RNA synthesis
  作者：Prakash C. Joshi、Michael F. Aldersley、James P. Ferris

  DOI：10.1016/j.bbrc.2011.09.008

  日期：2011.10

  The Na(+)-montmorillonite-catalyzed reactions of 5'-phosphorimidazolides of nucleosides generates RNA oligomers. The question arises as to how chiral selectivity was introduced into this biopolymer from a simple chemical system. We have demonstrated homochiral selection in quaternary reactions of a racemic mixture of D,L-ImpA and D,L-ImpU on Na(+)-montmorillonite. The dimer, trimer, tetramer and pentamer

  Na（+）-蒙脱石催化的核苷5'-磷酰胺基咪唑化物反应可生成RNA低聚物。问题是如何通过简单的化学系统将手性选择性引入该生物聚合物。我们已经证明了在Na（+）-蒙脱石上D，L-ImpA和D，L-ImpU的外消旋混合物的四级反应的同手性选择。研究了二聚体，三聚体，四聚体和五聚体级分的同手性选择。通过离子交换HPLC收集产物，其末端5'-磷酸被碱性磷酸酶切割。通过反相HPLC分析这些级分，以鉴定同手性和杂手性异构体。受二聚体（63.5±0.8％）和三聚体（74.3±1.7％）的均一手性过量的鼓励，该研究扩展到了高级低聚物的分析。四元反应的四聚体和五聚体在反相柱上分别分离为26和22个异构体。它们与d-ImpA和D-ImpU在Na（+）蒙脱土上的二元反应形成的共洗脱分别显示四聚体和五聚体的92.7±2.0％和97.2±0.5％的手性。这些结果表明，Na（+）-蒙脱石不仅催化RNA的益生元合成，而且还促进同手性的选择。
• 一种P2Y2受体激动剂地夸磷索四钠的制备方法
  申请人：中国药科大学

  公开号：CN111454312A

  公开（公告）日：2020-07-28

  本发明公开了一种P2Y2受体激动剂地夸磷索四钠的制备方法，式II所示的焦磷酸化合物与长链有机胺成盐得到化合物式III，进而经过羰基二咪唑活化得到焦磷酸活性化合物式IV，式V所示的尿苷单磷酸化合物与长链有机胺成盐得到化合物式VI，最后，式IV与式VI经过Lewis酸催化，在亲水性溶剂中进行反应，得到式I所示的目标产物地夸磷索四钠。本方法使用阳离子交换树脂处理价格低廉且易得易保存的反应原料以及使用有机碱与反应原料成盐提高其受热稳定性，最后通过阴离子交换色谱法纯化得到目标产品。该方法高效，产品易分离，收率高。
• Methods for modulating taste receptors
  申请人：MARS, INCORPORATED

  公开号：US11185100B2

  公开（公告）日：2021-11-30

  Amino acids present in domains of an umami taste receptor are described herein, wherein the amino acids interact with at least one nucleotide derivative and/or at least one transmembrane compound that potentiates, modulates, increases, and/or enhances the activity of the umami receptor. Such compounds can be used in flavor compositions to enhance the umami taste and/or palatability of food products.

  本文描述了存在于鲜味受体结构域中的氨基酸，其中氨基酸与至少一种核苷酸衍生物和/或至少一种跨膜化合物相互作用，从而增强、调节、增加和/或提高鲜味受体的活性。此类化合物可用于调味组合物，以增强食品的鲜味和/或适口性。
• 1,8-Naphthalimide-based colorimetric and fluorescent sensor for recognition of GMP, TMP, and UMP and its application in in vivo imaging
  作者：Li Mei Zhang、Lin E. Guo、Xue Mei Li、Yong Gang Shi、Gao Fen Wu、Xiao Guang Xie、Ying Zhou、Qi Hua Zhao、Jun Feng Zhang

  DOI：10.1016/j.tetlet.2014.09.074

  日期：2014.10

  In this study, a series of 1,8-naphthalimide-based analogs were developed for fluorescence imaging of nucleotides in Caenorhabditis elegans. In DMSO, compound 1 proved to be an effective and selective colorimetric and fluorescent sensor for recognition of GMP, TMP, and UMP over other structurally similar nucleotides. Among all the tested nucleotides, only the addition of GMP, TMP, and UMP resulted in a fluorescence color change from blue to brown with a fluorescence enhancement of more than 600-fold, with the colorless solution turning brown. NMR spectroscopic titration, theoretical calculations, and spectral tests performed using various solvent compositions confirmed that compound 1 formed multiple hydrogen bonds with the related base groups in the nucleotide. Compound 1 demonstrated its utility as a fluorescent chemosensor for detecting GMP, TMP, and UMP in in vivo imaging of GMP, TMP, and UMP in C elegans. (C) 2014 Elsevier Ltd. All rights reserved.