1-(β-D-erythrofuranosyl)uracil | 40653-40-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-(β-D-erythrofuranosyl)uracil
• 英文别名: Erythrofuranosyluridine；1-[(2R,3R,4R)-3,4-dihydroxyoxolan-2-yl]pyrimidine-2,4-dione
• CAS: 40653-40-5
• 化学式: C₈H₁₀N₂O₅
• 分子量: 214.178
• InChiKey: UIYGLPAAPTWXPZ-QPPQHZFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  99.1
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(β-D-erythrofuranosyl)uracil 生成 Acetic acid (R)-2-(2-acetoxy-ethoxy)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-ethyl ester
  参考文献：
  名称：

  ZAVGORODNIJ, S. G.;EFIMTSEVA, E. V.;MIXAJLOV, S. N.;TSILEVICH, T. L.;YAVO+, XIMIYA GETEROTSIKL. SOED.,(1988) N 2, 223-228

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(2',3'-di-O-acetyl-β-D-erythrofuranosyl)uracil 在 sodium hydroxide 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 0.13h， 以80%的产率得到1-(β-D-erythrofuranosyl)uracil
  参考文献：
  名称：

  具有包含核碱基的主链的寡核苷酸类似物：第 6 部分，2-脱氧-D-赤藓糖衍生的亚磷酰胺：合成和掺入 14-Mer DNA 链

  摘要：

  Two modified DNA 14-mers have been prepared, containing either a 2-deoxy-D-erythrose-derived adenosine analogue carrying a C(8)-CH2O group (deA*). or a 2-deoxy-D-erpthrose-derived uridine analogue, possessing a C(6)-CH2O group (deU*). These nucleosides are linked via a phosphinato group between O-C(3') (deA* and deU*) and O-C(5') of one neighbouring nucleotide, and between C(8)-CH2O (deA*),or C(6)-CH2O (deU*) and O-C(3') of the second neighbour. N-6-Benzoyl-9-(beta -D-erythrofuranosyl)adeine (3) and 1-(beta -D-erythrofuranosyl)uracil (4) were prepared from D-glucose, deoxygenated at C(2'), and converted into the required phosphoramidites 1 and 2. The modified tetradecamers 31 and 32 were prepared by solid-phase synthesis. Pairing studies show a decrease in the melting temperature of 7 to 8 degrees for the duplexes 31 30 and 32 29, as compared to the unmodified DNA duplex 29 30. A comparison with the pairing properties of tetradecamers similarly incorporating deoxyribose- instead of the deoxyerythrose-derived nucleotides evidences that the CH2OH substituent at C(4') has no significant effect on the pairing.

  DOI：

  10.1002/1522-2675(20010516)84:5<1000::aid-hlca1000>3.0.co;2-s

文献信息

• Activation of Orotidine 5‘-Monophosphate Decarboxylase by Phosphite Dianion:  The Whole Substrate is the Sum of Two Parts
  作者：Tina L. Amyes、John P. Richard、James J. Tait

  DOI：10.1021/ja055493s

  日期：2005.11.1

  group of the natural substrate orotidine 5'-monophosphate (OMP). The data give kcat = 160 +/- 70 s-1 for turnover of EO in the active site of OMPDC containing phosphite dianion, which is significantly larger than kcat = 15 s-1 for turnover of OMP. Despite the weaker binding of the individual EO and HPO32- "parts" (KmKd = 0.014 M2) than of OMP (Km = 1.6 x 10-6 M), once bound, OMPDC provides a slightly

  我们报告说，亚磷酸二价阴离子与乳清酸 5'-单磷酸脱羧酶 (OMPDC) 的结合导致截断底物 1-(β-d-呋喃糖基) 乳清酸 (EO) 脱羧的 kcat/Km 增加了 80 000 倍)，缺少 5'-磷酸二价阴离子部分。过渡态亚磷酸酯二价阴离子的固有结合能 (IBE) 为 7.8 kcal/mol，占天然底物乳清酸 5'-单磷酸酯 (OMP) 磷酸二价阴离子基团 11.8 kcal/mol IBE 的很大一部分。数据表明，在含有亚磷酸酯二价阴离子的 OMPDC 活性位点中，EO 的周转率为 kcat = 160 +/- 70 s-1，明显大于 OMP 周转的 kcat = 15 s-1。尽管单个 EO 和 HPO32-“部分”（KmKd = 0.014 M2）的结合比 OMP（Km = 1.6 x 10-6 M）弱，一旦结合，OMPDC 为部分反应提供比整个底物稍大的过渡态稳定性。因此，
• Enzyme Architecture: The Activating Oxydianion Binding Domain for Orotidine 5′-Monophophate Decarboxylase
  作者：Krisztina Spong、Tina L. Amyes、John P. Richard

  DOI：10.1021/ja4107513

  日期：2013.12.11

  Orotidine 5'-monophosphate decarboxylase catalyzes the decarboxylation of truncated substrate (1-β-D-erythrofuranosyl)orotic acid to form (1-β-D-erythrofuranosyl)uracil. This enzyme-catalyzed reaction is activated by tetrahedral oxydianions, which bind weakly to unliganded OMPDC and tightly to the enzyme-transition state complex, with the following intrinsic oxydianion binding energies (kcal/mol):

  乳清酸 5'-单磷酸脱羧酶催化截短的底物（1-β-D-呋喃红糖基）乳清酸脱羧形成（1-β-D-呋喃红糖基）尿嘧啶。这种酶催化反应由四面体氧二阴离子激活，四面体氧二阴离子与未配位的 OMPDC 弱结合并与酶-过渡态复合物紧密结合，具有以下固有氧二阴离子结合能（kcal/mol）：SO3(2-), -8.3；HPO3(2-)，-7.7；S2O3(2-)，-4.6；SO4(2-)，-4.5；HOPO3(2-), -3.0; HOAsO3(2-)，未检测到激活。我们提出 OMPDC 的氧双阴离子和乳清酸结合域在催化脱羧反应中发挥互补作用：（1）乳清酸结合域进行乳清酸环的脱羧。
• (13C)-Substituted erythronucleosides: synthesis and conformational analysis by proton and carbon-13 NMR spectroscopy
  作者：Paul C. Kline、Anthony S. Serianni

  DOI：10.1021/jo00032a032

  日期：1992.3

  The erythronucleosides, 9-beta-D-erythrofuranosyladenine (1b), 1-beta-D-erythrofuranosylcytosine (2b), 9-beta-D-erythrofuranosylguanine (3b), and 1-beta-D-erythrofuranosyluracil (4b), were synthesized with and without C-13-substitution at C1' of the furanose ring. 75-MHz C-13 and 620-MHz H-1 NMR spectra of 1-4b were interpreted, in the latter case with the assistance of spectral simulation, and H-1-H-1, C-13-H-1, and C-13-C-13 spin couplings were used to assess furanose conformation. 3J(HH) data in (H2O)-H-2 were treated by computer to determine the preferred north and south conformers, their puckering amplitudes, and their mole fractions in solution, and J(CH) data were used to complement this analysis. A similar treatment of spin coupling data for the corresponding ribonucleosides 1-4a was also conducted to permit a comparison of furanose conformations in both series of compounds. Results show that the removal of the exocyclic hydroxymethyl group from 1-4a, giving 1-4b, significantly enhances the proportion of south conformers in aqueous ((H2O)-H-2) solution.
• Disaccharide Pyrimidine Nucleosides and Their Derivatives: A Novel Group of Cell-Penetrating Inhibitors of Poly(ADP-Ribose) Polymerase 1
  作者：Anna S. Efremova、Alexandra L. Zakharenko、Stanislav I. Shram、Irina V. Kulikova、Mikhail S. Drenichev、Maria V. Sukhanova、Svetlana N. Khodyreva、Nikolay F. Myasoedov、Olga I. Lavrik、Sergey N. Mikhailov

  DOI：10.1080/15257770.2013.827793

  日期：2013.9.2

  Nearly 30 synthetic nucleosides were tested with human recombinant poly(ADP-ribose) polymerase 1 as potential inhibitors of this enzyme. The most active compounds were some disaccharide analogues of thymidine: 3-O-beta-D-ribofuranosyl-5-iodo-dUrd (2d; IC50 = 45 mu M), 3-O-beta-D-ribofuranosyl-2-deoxythymidine (2e; IC50 = 38M), and 3-O-beta-D-ribofuranosyl-2-deoxythymidine oxidized (4; IC50 = 25 mu M). These compounds also reduced H2O2-induced synthesis of poly(ADP-ribose) in cultured human ovarian carcinoma (SKOV-3) cells in a dose-dependent manner. Furthermore, compounds 2d or 2e until a concentration of 1mM did not affect growth of SKOV-3 cells, whereas dialdehyde compound 4, as well as thymidine, exhibited a significant cytotoxicity.
• Acyclic analogs of nucleosides. Synthesis of 1,5-dihydroxy-3-oxa-2-pentyl derivatives of nucleic bases
  作者：S. G. Zavgorodnii、E. V. Efimtseva、S. N. Mikhailov、T. L. Tsilevich、A. �. Yavorskii、V. L. Florent'ev

  DOI：10.1007/bf00473330

  日期：1988.2