2'-O-Methyl-5-methyl-2-thiouridine | 1229293-78-0

• 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: 2'-O-Methyl-5-methyl-2-thiouridine
• 英文别名: 2'-O-methyl-5-methyl-2thiouridine；1-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxyoxolan-2-yl]-5-methyl-2-sulfanylidenepyrimidin-4-one
• CAS: 1229293-78-0
• 化学式: C₁₁H₁₆N₂O₅S
• 分子量: 288.324
• InChiKey: RFMOGKGPQDPXQS-FDDDBJFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  123
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2'-O-Methyl-5-methyl-2-thiouridine 在 吡啶 、 四氮唑 、 氨 、 二异丙胺 、 三氯氧磷 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 12.0h， 生成 (2R,3R,4R,5R)-5-(4-amino-5-methyl-2-thioxopyrimidin-1(2H)-yl)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-methoxytetrahydrofuran-3-yl (2-cyanoethyl) diisopropylphosphoramidite
  参考文献：
  名称：

  Stable triplex formation using the strong stacking effect of consecutive thionucleoside moieties

  摘要：

  在本研究中，发现连续的硫代羰基团s2T和m5s2C的排列显著稳定了三链体中的预质子化形式，并且这种预质子化形式的稳定性增加了三链体中胞嘧啶衍生物的pKa值。

  DOI：

  10.1039/c1cc14339e
• 作为产物：
  描述：

  5-甲基尿甙 在 吡啶 、 三乙烯二胺 、 tetraphosphorus decasulfide 、 (Z)-2-nitrobenzaldehyde oxime 、 四丁基溴化铵 、 sodium hydride 、 sodium carbonate 、 potassium carbonate 、 triethylamine tris(hydrogen fluoride) 、 三乙胺 、 四甲基胍 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 26.66h， 生成 2'-O-Methyl-5-methyl-2-thiouridine
  参考文献：
  名称：

  Stable triplex formation using the strong stacking effect of consecutive thionucleoside moieties

  摘要：

  在本研究中，发现连续的硫代羰基团s2T和m5s2C的排列显著稳定了三链体中的预质子化形式，并且这种预质子化形式的稳定性增加了三链体中胞嘧啶衍生物的pKa值。

  DOI：

  10.1039/c1cc14339e

文献信息

• Oligoribonucleotides and ribonucleases for cleaving RNA
  申请人：Isis Pharmaceuticals, Inc.

  公开号：US06107094A1

  公开（公告）日：2000-08-22

  Oligomeric compounds including oligoribonucleotides and oligoribonucleosides are provided that have subsequences of 2'-pentoribofuranosyl nucleosides that activate dsRNase. The oligoribonucleotides and oligoribonucleosides can include substituent groups for increasing binding affinity to complementary nucleic acid strand as well as substituent groups for increasing nuclease resistance. The oligomeric compounds are useful for diagnostics and other research purposes, for modulating the expression of a protein in organisms, and for the diagnosis, detection and treatment of other conditions susceptible to oligonucleotide therapeutics. Also included in the invention are mammalian ribonucleases, i.e., enzymes that degrade RNA, and substrates for such ribonucleases. Such a ribonuclease is referred to herein as a dsRNase, wherein "ds" indicates the RNase's specificity for certain double-stranded RNA substrates. The artificial substrates for the dsRNases described herein are useful in preparing affinity matrices for purifying mammalian ribonuclease as well as non-degradative RNA-binding proteins.

  提供了包括寡核苷酸和寡核苷在内的寡聚合物化合物，其具有激活双链RNA酶的2'-戊核糖核苷亚序列。这些寡核苷酸和寡核苷可以包括取代基团，用于增加与互补核酸链的结合亲和力，以及用于增加核酸酶抗性的取代基团。这些寡聚合物化合物对于诊断和其他研究目的、调节生物体中蛋白质表达以及对易受寡核苷酸治疗的其他疾病进行诊断、检测和治疗都是有用的。该发明还包括哺乳动物核酸酶，即降解RNA的酶，以及这些核酸酶的底物。这样的核酸酶在此处被称为双链RNA酶，其中“ds”表示RNase对特定双链RNA底物的特异性。此处描述的双链RNA酶的人工底物对于制备亲和基质以纯化哺乳动物核酸酶以及非降解RNA结合蛋白是有用的。
• Oligoribonucleotides for cleaving RNA
  申请人：ISIS Pharmaceuticals, Inc.

  公开号：US05898031A1

  公开（公告）日：1999-04-27

  Oligomeric compounds including oligoribonucleotides and oligoribonucleosides are provided that have subsequences of 2-pentoribofuranosyl nucleosides that activate dsRNase. The oligoribonucleotides and oligoribonucleosides can include substituent groups for increasing binding affinity to complementary nucleic acid strand as well as substituent groups for increasing nuclease resistance. The oligomeric compounds are useful for diagnostics and other research purposes, for modulating the expression of a protein in organisms, and for the diagnosis, detection and treatment of other conditions susceptible to oligonucleotide therapeutics.

  提供了包括寡核糖核苷酸和寡核糖核苷在内的寡聚化合物，其中包含激活双链RNA酶的2-戊核糖呋喃核苷亚序列。这些寡核糖核苷酸和寡核糖核苷可以包括取代基团，用于增加与互补核酸链的结合亲和力，以及用于增加核酸酶抵抗力的取代基团。这些寡聚化合物对于诊断和其他研究目的、调节生物体中蛋白质表达以及对易感于寡核苷酸治疗的其他状况的诊断、检测和治疗都是有用的。
• Process for the synthesis of 2′-O-substituted pyrimidines and oligomeric compounds therefrom
  申请人：Isis Pharmaceuticals, Inc.

  公开号：US06222025B1

  公开（公告）日：2001-04-24

  Oligonucleotide analogs are disclosed having pyrimidine monomeric sub-units therein that are modified at the 2′ and 5 positions. Monomeric sub-units having these modifications may be further modified at the 2 position. Improved processes for the synthesis of 2′-O-substituted pyrimidine nucleosides are also provided. The processes feature alkylation of a 2,2′-anhydropyrimidine nucleoside or a 2S,2′-anhydropyrimidine nucleoside with a weak nucleophile in the presence of a Lewis acid.

  披露了含有嘧啶单体亚单位的寡核苷酸类似物，其中在2′和5位点进行了修饰。具有这些修饰的单体亚单位可以在2位点进一步修饰。还提供了改进的合成2′-O-取代嘧啶核苷的过程。这些过程包括在Lewis酸存在下使用弱亲核试剂烷基化2,2′-脱水嘧啶核苷或2S,2′-脱水嘧啶核苷。
• Process for the synthesis of 2'-O-substituted pyrimidines
  申请人：Isis Pharmaceuticals, Inc.

  公开号：US05760202A1

  公开（公告）日：1998-06-02

  Improved processes for the synthesis of 2'-O-substituted pyrimidine nucleosides are provided. The processes feature alkylation of a 2,2'-anhydropyrimidine nucleoside or a 2S,2'-anhydropyrimidine nucleoside with a weak nucleophile in the presence of a Lewis acid.

  提供了合成2'-O取代嘧啶核苷的改进工艺。该工艺采用2,2'-无水嘧啶核苷或2S,2'-无水嘧啶核苷与弱亲核试剂在路易斯酸存在下进行烷基化反应。
• Process for the synthesis of 2' -O-substituted pyrimidines and oligomeric compounds therefrom
  申请人：ISIS Pharmaceuticals, Inc.

  公开号：US20030050454A1

  公开（公告）日：2003-03-13

  oligonucleotide analogs are disclosed having pyrimidine monomeric sub-units therein that are modified at the 2′ and 5′ positions. Monomeric sub-units having these modifications may be further modified at the 2′ position. Improved processes for the synthesis of 2′-O-substituted pyrimidine nucleosides are also provided. The processes feature alkylation of a 2,2′-anhydropyrimidine nucleoside or a 2S,2′-anhydropyrimidine nucleoside with a weak nucleophile in the presence of a Lewis acid.

  本文披露了含有嘧啶单体亚基的寡核苷酸类似物，其在2'和5'位置进行了修饰。具有这些修饰的单体亚基可以进一步在2'位置进行修饰。还提供了改进的2'-O-取代嘧啶核苷合成过程。该过程采用弱亲核试剂在Lewis酸存在下与2,2'-脱水嘧啶核苷或2S,2'-脱水嘧啶核苷烷基化的方法。