1-β-D-ribofuranosyl-5,6-dimethyluracil | 16710-16-0

• 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: 1-β-D-ribofuranosyl-5,6-dimethyluracil
• 英文别名: 5,6-dimethyl-uridine；5,6-Dimethyl-uridin；5,6-Dimethyluridine；1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5,6-dimethylpyrimidine-2,4-dione
• CAS: 16710-16-0
• 化学式: C₁₁H₁₆N₂O₆
• 分子量: 272.258
• InChiKey: CUJCOVAXFZKIAJ-FDDDBJFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  119
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-β-D-ribofuranosyl-5,6-dimethyluracil 在 吡啶 、 silver nitrate 作用下， 以 四氢呋喃 为溶剂， 生成 5'-O-4,4'-dimethoxytrityl-3'-O-tert-butyldimethylsilyl-5,6-dimethyluridine
  参考文献：
  名称：

  Synthesis and Properties of Uniquely Modified Oligoribonucleotides: Yeast Trna^PheFragments with 6-Methyluridine and 5,6-Dimethyluridine at Site-Specific Positions

  摘要：

  The phosphoramidites of 6-methyluridine and 5,6-dimethyluridine were synthesized and the modified uridines site-selectively incorporated into heptadecamers corresponding in sequence to the yeast tRNA(Phe) anticodon and T Psi C domains. The oligoribonucleotides were characterized by NMR, MALDI-TOF MS and UV-monitored thermal denaturations. The 6-methylated uridines retained the syn conformation at the polymer level and in each sequence location destabilized the RNAs compared to that of the unmodified RNA. The decrease in RNA duplex stability is predictable. However, loss of stability when the modified uridine is in a loop is sequence context dependent, and can not, at this time, be predicted from the location in the loop.

  DOI：

  10.1080/15257770008035004
• 作为产物：
  描述：

  1-乙酰氧基-2,3,5-三苯甲酰氧基-1-beta-D-呋喃核糖 在 甲醇 、 三氟甲磺酸三甲基硅酯 、 sodium methylate 、 三氟乙酸 作用下， 以 乙腈 为溶剂， 反应 24.5h， 生成 1-β-D-ribofuranosyl-5,6-dimethyluracil
  参考文献：
  名称：

  尿苷的6-取代和5,6-二取代衍生物：立体选择性合成，与尿苷磷酸化酶的相互作用以及体外抗肿瘤活性。

  摘要：

  描述了通过路易斯酸催化的（a）三甲基硅烷化的6-烷基-4-烷基硫尿嘧啶与1-O-乙酰基-2,3,5-三-O-苯甲酰基-β-的缩合反应合成6-烷基尿苷的立体选择程序。 D-核呋喃糖（ABR）和（b）三甲基甲硅烷基化的6-烷基-3-苄基尿嘧啶与ABR。随后通过使用配合物BBr3-THF的新的改性方法，使用1N三氟乙酸除去4-甲硫基，并除去3-苄基。此外，通过依次用SeO 2氧化并用四丁基硼氢化铵还原6-甲基尿苷（5）获得6-（羟甲基）尿苷（39）和5-氟-6-（羟甲基）尿苷（40）。分别通过39和40的DAST处理，获得了5-氟-6-甲基尿苷和3-氟-6-甲基尿苷（35），以及它们相应的6-氟甲基同源物41和42。对于前述关于糖基键的固定顺式构象的所有核苷，1 H NMR光谱进一步证实戊糖环主要存在于构象N（3'-内）。大多数核苷是大肠杆菌嘧啶核苷磷酸化酶的弱底物。其中两个39和41具有6-C

  DOI：

  10.1021/jm950675q

文献信息

• OLIGONUCLEOTIDE
  申请人：Kyowa Hakko Kirin Co., Ltd.

  公开号：EP2891717A1

  公开（公告）日：2015-07-08

  The present invention provides an oligonucleotide having improved affinity for AG02, and the like. The oligonucleotide has a nucleotide residue or a nucleoside residue represented by formula (I) wherein X1 is an oxygen atom or the like, R1 is formula (IIA) (wherein R5A is halogen or the like, and R6A is a hydrogen atom or the like) or formula (IVA) (wherein Y3A is a nitrogen atom or the like, and Y4A is CH or the like), or the like, R2 is a hydrogen atom, hydroxy, halogen, or optionally substituted lower alkoxy, and R3 is a hydrogen atom or the like} at the 5' end thereof, and the nucleotide residue or the nucleoside residue binds to an adjacent nucleotide residue through the oxygen atom at position 3.

  本发明提供了一种对 AG02 等具有更好亲和力的寡核苷酸。该寡核苷酸具有由式（I）代表的核苷酸残基或核苷残基其中 X1 是氧原子或类似物，R1 是式（IIA）（其中 R5A 是卤素或类似物，R6A 是氢原子或类似物）或式（IVA）（其中 Y3A 是氮原子或类似物、或类似物），R2 是氢原子、羟基、卤素或任选取代的低级烷氧基，R3 是氢原子或类似物}在其 5'端，核苷酸残基或核苷酸残基通过位置 3 的氧原子与相邻的核苷酸残基结合。
• 6-Substituted and 5,6-Disubstituted Derivatives of Uridine:  Stereoselective Synthesis, Interaction with Uridine Phosphorylase, and <i>in Vitro</i> Antitumor Activity
  作者：Krzysztof Felczak、Alicja K. Drabikowska、Juhani A. Vilpo、Tadeusz Kulikowski、David Shugar

  DOI：10.1021/jm950675q

  日期：1996.1.1

  hydrogen bond with the enzyme. The 5-fluoro-6-substituted uridines were the poorest substrates. Cytotoxicities of the nucleosides were examined vs the human tumor cell lines MOLT-3, U-937, K-562, and IM-9, as well as PHA-stimulated human lymphocytes. Two of the analogues, 5-fluoro-6-(fluoromethyl)uridine (42) and 5-fluoro-6-(hydroxymethyl)uridine (40), exhibited cytotoxicities comparable to that of 5-fluorouracil

  描述了通过路易斯酸催化的（a）三甲基硅烷化的6-烷基-4-烷基硫尿嘧啶与1-O-乙酰基-2,3,5-三-O-苯甲酰基-β-的缩合反应合成6-烷基尿苷的立体选择程序。 D-核呋喃糖（ABR）和（b）三甲基甲硅烷基化的6-烷基-3-苄基尿嘧啶与ABR。随后通过使用配合物BBr3-THF的新的改性方法，使用1N三氟乙酸除去4-甲硫基，并除去3-苄基。此外，通过依次用SeO 2氧化并用四丁基硼氢化铵还原6-甲基尿苷（5）获得6-（羟甲基）尿苷（39）和5-氟-6-（羟甲基）尿苷（40）。分别通过39和40的DAST处理，获得了5-氟-6-甲基尿苷和3-氟-6-甲基尿苷（35），以及它们相应的6-氟甲基同源物41和42。对于前述关于糖基键的固定顺式构象的所有核苷，1 H NMR光谱进一步证实戊糖环主要存在于构象N（3'-内）。大多数核苷是大肠杆菌嘧啶核苷磷酸化酶的弱底物。其中两个39和41具有6-C
• Synthesis and Properties of Uniquely Modified Oligoribonucleotides: Yeast Trna^PheFragments with 6-Methyluridine and 5,6-Dimethyluridine at Site-Specific Positions
  作者：Elzbieta Sochacka、Grazyna Czerwinska、Richard Guenther、Robert Cain、Paul F. Agris、Andrzej Malkiewicz

  DOI：10.1080/15257770008035004

  日期：2000.3

  The phosphoramidites of 6-methyluridine and 5,6-dimethyluridine were synthesized and the modified uridines site-selectively incorporated into heptadecamers corresponding in sequence to the yeast tRNA(Phe) anticodon and T Psi C domains. The oligoribonucleotides were characterized by NMR, MALDI-TOF MS and UV-monitored thermal denaturations. The 6-methylated uridines retained the syn conformation at the polymer level and in each sequence location destabilized the RNAs compared to that of the unmodified RNA. The decrease in RNA duplex stability is predictable. However, loss of stability when the modified uridine is in a loop is sequence context dependent, and can not, at this time, be predicted from the location in the loop.