3-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-2(1H)-one | 136505-59-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-2(1H)-one
• 英文别名: 3-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-pyridin-2-one
• CAS: 136505-59-4
• 化学式: C₁₀H₁₃NO₄
• 分子量: 211.218
• InChiKey: YNJXVLYVDHPJSP-DJLDLDEBSA-N

物化性质

• 熔点：
  115-116 °C
• 沸点：
  560.9±50.0 °C(Predicted)
• 密度：
  1.384±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  78.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-2(1H)-one 在 咪唑 、 Amberlite IRC-50H+ 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.5h， 生成 3-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-1H-pyridin-2-one
  参考文献：
  名称：

  Chemical synthesis and characterization of duplex DNA containing a new base pair: a nondisruptive, benzofused pyrimidine analog

  摘要：

  A new base pair appropriate for incorporation into B-DNA was designed with the goal of allowing fusion of a benzene substituent across the 4 and 5 carbons of a pyrimidine analog. Such a residue may have utility in the preparation of DNA duplexes bearing precisely spatially positioned and conformationally constrained unnatural substituents such as reporter groups. The design called for the incorporation of the beta-anomer of a C-linked deoxyriboside of 2-hydroxyquinoline (dQ) opposite the beta-N9 deoxyriboside of 2-aminopurine (dAP). Several duplex DNAs were synthesized containing this new base pair as well as the analog in which 2-hydroxypyridine replaces 2-hydroxyquinoline (dP). Phosphoramidites 17 and 18 were synthesized and incorporated into synthetic oligonucleotides using automated methodology. That dQ and dP had been incorporated without chemical modification was proven by enzymatic digestion of the synthetic oligonucleotides to the component nucleosides and analysis by HPLC. Native polyacrylamide gel electrophoresis revealed that admixture of complementary strands containing dP or dQ opposite dAP gave new substances with mobility comparable to a duplex DNA of the same length containing only Watson-Crick base pairs. Solution circular dichroism measurements were consistent with these substances existing in the B conformation. T(m), DELTAH, and DELTAS were measured for synthetic duplex DNAs containing pairings of dQ and dP with dAP, dA, dC, dG, and dT. Of these, duplexes in which dAP was the partner of dP or dQ were most thermodynamically stable (DELTAG 25-degrees-C) and highest melting, with T(m) values lower by 1 to 5-degrees-C than the corresponding dA.dT-containing duplex. Solution H-1 NMR measurements from delta 11-15 on an 11-mer duplex containing the dAP.dQ pair were diagnostic for the presence of 11 base pairs. The resonance for the dAP-dQ base pair was assigned on the basis of a combination of 1D NOE measurements, temperature-dependent line width, and chemical shift measurements. We conclude that dP and dQ are competent base-pairing partners for dAP in duplex DNA and are reasonable condidates for use in the design of novel base-pairing nucleoside analogs.

  DOI：

  10.1021/jo00060a045
• 作为产物：
  描述：

  1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol 在 氢氧化钾 、 碘代三甲硅烷 、 氨 、 臭氧 、 三乙胺 、 三苯基膦 、 三氟乙酸 、 偶氮二甲酸二乙酯 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 2.0h， 生成 3-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-2(1H)-one
  参考文献：
  名称：

  Stereocontrolled syntheses of C-linked deoxyribosides of 2-hydroxypyridine and 2-hydroxyquinoline

  摘要：

  2'-Deoxy-C-ribosides 4 and 5 were prepared in optically active form by a route expected to be generally useful for the synthesis of the alpha- or beta-anomers of 2'-deoxy-C-ribosides. Key steps are the addition of an organometallic reagent to aldehyde 7, mesylation of the resulting alcohol, and stereospecific deprotection/cyclization to yield the 2'-deoxy-C-riboside (7 + 8 --> 9/10; 9 --> 11).

  DOI：

  10.1016/s0040-4039(00)92690-x

文献信息

• Synthesis of 6-Substituted 2(1H)-Pyridon-3-yl C-2′-Deoxyribonucleosides
  作者：Hubert Chapuis、Tomáš Kubelka、Nicolas Joubert、Radek Pohl、Michal Hocek

  DOI：10.1002/ejoc.201101662

  日期：2012.3

  Two approaches to the synthesis of the title 6-substituted 2(1H)-pyridon-3-yl C-2′-deoxyribonucleosides have been pursued. A protected 6-aminopyridine C-nucleoside intermediate was converted into the N-oxide followed by Ac2O-mediated rearrangement and final deprotection to give 6-acetylamino-2-oxo(1H)-pyridin-3-yl deoxyribonucleoside. Due to the unusually high stability of the N-acetyl group, the full

  已探索了两种合成标题 6-取代的 2(1H)-pyridon-3-yl C-2'-脱氧核糖核苷的方法。受保护的 6-氨基吡啶 C-核苷中间体被转化为 N-氧化物，然后是 Ac2O 介导的重排和最终脱保护，得到 6-乙酰氨基-2-氧代 (1H)-吡啶-3-基脱氧核糖核苷。由于 N-乙酰基异常高的稳定性，完全脱保护没有成功。在第二种方法中，6-氯-2-吡啶酮被转化为二酰胺磷酸酯，其经历邻位镁化和碘化得到3-碘衍生物。然后将其与糖醛进行 Heck 偶联，所得产物脱保护得到 6-氯-2-氧代 (1H)-吡啶-3-基脱氧核糖核苷，其直接或再保护后转化为 6-甲基- , 6-氨基-, 和 6-未取代的吡啶酮 C-核苷。最终的核苷非常不稳定，容易差向异构化和/或氧化，这限制了（但不排除）它们在化学生物学中的进一步应用。
• Nucleoside or nucleotides having novel unnatural bases and utilization of the same
  申请人：Hirao Ichiro

  公开号：US20060263771A1

  公开（公告）日：2006-11-23

  The object of the present invention is to provide a nucleoside or nucleotide having an unnatural base. The nucleoside or nucleotide of the present invention has a 5-substituted-2-oxo(1H)-pyridin-3-yl group as a base. Preferably, the 5-position of the above base is substituted with a substituent selected from the group consisting of the following: 1) a photoreactive group selected from iodine and bromine; 2) an alkenyl group, an alkynyl group or an amino group, or a derivative thereof; 3) biotin or a derivative thereof; and 4) a fluorescent molecule selected from fluorescein, 6-carboxyfluorescein, tetramethyl-6-carboxyrhodamine, and derivatives thereof.

  本发明的目的是提供一种具有非天然碱基的核苷或核苷酸。本发明的核苷或核苷酸具有5-取代-2-氧代（1H）-吡啶-3-基团作为碱基。优选地，上述碱基的5位被取代为以下群组中选择的取代基：1）光敏反应基团，选择自碘和溴；2）烯基基团，炔基基团或氨基基团或其衍生物；3）生物素或其衍生物；和4）荧光分子，选择自荧光素，6-羧基荧光素，四甲基-6-羧基罗丹明和其衍生物。
• [EN] OLIGONUCLEOTIDE COMPOSITIONS AND METHODS THEREOF<br/>[FR] COMPOSITIONS D'OLIGONUCLÉOTIDES ET PROCÉDÉS ASSOCIÉS
  申请人：WAVE LIFE SCIENCES LTD

  公开号：WO2022099159A1

  公开（公告）日：2022-05-12

  Among other things, the present disclosure provides oligonucleotides and compositions thereof. In some embodiments, provided oligonucleotides and compositions are useful for adenosine modification. In some embodiments, the present disclosure provides methods for treating various conditions, disorders or diseases that can benefit from adenosine modification.

  除其他事项外，本公开提供寡核苷酸及其组合物。在某些实施例中，提供的寡核苷酸及其组合物对腺苷修饰有用。在某些实施例中，本公开提供了治疗各种需要腺苷修饰的疾病、疾病或病症的方法。
• NOVEL NUCLEOSIDE OR NUCLEOTIDE DERIVATIVE AND USE THEREOF
  申请人：Riken

  公开号：EP1816130A1

  公开（公告）日：2007-08-08

  The object of the present invention is to provide a nucleoside or nucleotide having a 5-substituted-2-oxo(1H)pyridin-3-yl group as a base, as well as a method using the same. In one embodiment, the nucleoside or nucleotide of the present invention has a fluorescent dye selected from the group consisting of 5-FAM, 6-FAM, 5-TAMRA, 6-TAMRA, DANSYL, 5-HEX, 6-HEX, 5-TET, 6-TET, 5-ROX and 6-ROX or a quencher dye selected from the group consisting of DABCYL. BHQ1 and BHQ2, which is attached either directly or through a linker to the 5-position of the above base.

  本发明的目的是提供一种以5-取代-2-氧代(1H)吡啶-3-基团为碱基的核苷或核苷酸，以及使用这种核苷或核苷酸的方法。 在一个实施方案中，本发明的核苷或核苷酸具有选自 5-FAM、6-FAM、5-TAMRA、6-TAMRA、DANSYL、5-HEX、6-HEX、5-TET、6-TET、5-ROX 和 6-ROX 组成的组的荧光染料或选自 DABCYL.BHQ1 和 BHQ2，它们直接或通过连接体连接到上述碱基的 5 位。
• Stereocontrolled syntheses of C-linked deoxyribosides of 2-hydroxypyridine and 2-hydroxyquinoline
  作者：Marjorie S. Solomon、Paul B. Hopkins

  DOI：10.1016/s0040-4039(00)92690-x

  日期：1991.7

  2'-Deoxy-C-ribosides 4 and 5 were prepared in optically active form by a route expected to be generally useful for the synthesis of the alpha- or beta-anomers of 2'-deoxy-C-ribosides. Key steps are the addition of an organometallic reagent to aldehyde 7, mesylation of the resulting alcohol, and stereospecific deprotection/cyclization to yield the 2'-deoxy-C-riboside (7 + 8 --> 9/10; 9 --> 11).