1-(2',3'-di-O-acetyl-β-D-erythrofuranosyl)uracil | 63709-22-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2',3'-di-O-acetyl-β-D-erythrofuranosyl)uracil
• 英文别名: 1-(2,3-di-O-acetyl-β-D-erythrofuranosyl)uracil
• CAS: 63709-22-8
• 化学式: C₁₂H₁₄N₂O₇
• 分子量: 298.252
• InChiKey: GXRFHQHWGCTXOL-FBIMIBRVSA-N

物化性质

• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.07
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  116.69
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1-(2',3'-di-O-acetyl-β-D-erythrofuranosyl)uracil 在 吡啶 、 碳酸二苯酯 、 sodium hydroxide 、 偶氮二异丁腈 、 三氟化硼乙醚 、 四丁基氟化铵 、 水 、 三正丁基氢锡 、 lithium bromide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 36.63h， 生成 1-(2'-deoxy-β-D-glycero-tetrofuranosyl)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
• 作为产物：
  描述：

  2,3,4-呋喃三醇,四氢-,三乙酸酯,(3R,4R)- 、 尿嘧啶 在 N,O-双三甲硅基乙酰胺 、 四氯化锡 作用下， 以 乙腈 为溶剂， 反应 0.83h， 以80%的产率得到1-(2',3'-di-O-acetyl-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，
• (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.