3'-azido-3'-deoxy-thymidine-5'-carboxylic acid | 146426-54-2

• 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: 3'-azido-3'-deoxy-thymidine-5'-carboxylic acid
• 英文别名: 3'-azido-thymidine-5'-carboxylic acid；4’-carboxylic acid-3’-azido-3’-deoxythymidine；4’-carboxylic acid-3’-deoxy-3’-azidothymidine；(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolane-2-carboxylic acid
• CAS: 146426-54-2
• 化学式: C₁₀H₁₁N₅O₅
• 分子量: 281.228
• InChiKey: YPULTFJGCRVCPG-XVMARJQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3'-azido-3'-deoxy-thymidine-5'-carboxylic acid 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N-甲基吡咯烷酮 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.17h， 生成
  参考文献：
  名称：

  An Entry of the Chemoselective Sulfo-Click Reaction into the Sphere of Nucleic Acids

  摘要：

  We report here the first example of a sulfo-click conjugation reaction to be applied to modified nucleosides. The reaction, which proceeds rapidly (k similar to 2.0 x 10(-1) M-1 s(-1) at 25 degrees C) under aqueous biocompatible conditions in the ribo- and deoxyribonucleoside series, affords the corresponding conjugated products in excellent yields. Furthermore, we demonstrate the orthogonality of the reaction with the copper-catalyzed azide-alkyne click reaction (CuAAC) by performing a one-pot dual labeling of a nucleoside carrying two orthogonal azido groups.

  DOI：

  10.1021/acs.orglett.0c00265
• 作为产物：
  描述：

  齐多夫定 在 ruthenium trichloride 、 氢氧化钾 、 dipotassium peroxodisulfate 作用下， 反应 3.0h， 以80%的产率得到3'-azido-3'-deoxy-thymidine-5'-carboxylic acid
  参考文献：
  名称：

  四氧化钌催化的核苷氧化：5'-羧酸衍生物的简便合成

  摘要：

  在碱性条件下，使用过硫酸钾和三氯化钌已将嘌呤和嘧啶核苷氧化为相应的5'-羧酸。所述方法提供了容易地从3'-叠氮基化合物接近带有3'-氨基和5'-羧酸官能团的核苷的例子，例如AZT的氧化然后酸的还原。

  DOI：

  10.1016/0040-4039(93)88026-f

文献信息

• Novel helical foldamers: organized heterogeneous backbone folding in 1 : 1 α/nucleoside-derived-β-amino acid sequences
  作者：Srivari Chandrasekhar、Nayani Kiranmai、Marelli Udaya Kiran、Ambure Sharada Devi、Gangireddy Pavan Kumar Reddy、Mohammed Idris、Bharatam Jagadeesh

  DOI：10.1039/c0cc01724h

  日期：——

  Secondary structural conformation of hybrid oligo-peptides comprised of 1 : 1 alternating Nucleoside Derived β-Amino acid (NDA) and L-amino acid residues has been reported. The studies reveal that the NDA residues organize the heterogeneous backbone featuring the surface properties of both nucleic acids and peptides, to adopt a novel 11/8-helical fold.

  杂合寡肽的二级结构构象由 1–:–1 交替核苷衍生的 β-氨基酸 (NDA) 和 L-氨基酸残基组成，已有报道。研究表明，NDA 残基组织了具有核酸和肽表面特性的异质主链，采用新型 11/8 螺旋折叠。
• Direct Access to Unique C‐5’‐Acyl Modified Nucleosides through Liebeskind–Srogl Cross‐Coupling Reaction
  作者：Mary Anne Maverick、Marie Gaillard、Jean‐Jacques Vasseur、Françoise Debart、Michael Smietana

  DOI：10.1002/ejoc.202101061

  日期：2022.6.7

  An efficient palladium/CuTC cocatalyzed cross-coupling reaction procedure for the synthesis of C-5’-acyl nucleosides from the corresponding nucleoside 5′-carbothioates and boronic acids is described. The procedure is fast, efficient, and it tolerates a wide variety of functionalities, thus expanding the so far limited chemical methods for C-5’ diversification of deoxy- and ribonucleosides.

  描述了一种有效的钯/CuTC 共催化交叉偶联反应程序，用于从相应的核苷 5'-硫代硫代糖酸酯和硼酸合成 C-5'-酰基核苷。该程序快速、高效，并且具有多种功能，从而扩展了迄今为止有限的 C-5' 脱氧和核糖核苷多样化的化学方法。
• Chimeric (α-amino acid + nucleoside-β-amino acid)_npeptide oligomers show sequence specific DNA/RNA recognition
  作者：Khirud Gogoi、Vaijayanti A. Kumar

  DOI：10.1039/b716835g

  日期：——

  An α/β-peptide backbone oligonucleotide comprising natural α-amino acids alternating with a β-amino acid component derived from thymidine sequence specifically recognizes and binds to deoxy- and ribo-oligoadenylates in triplex mode.

  α/β-肽主链寡核苷酸包含天然α-氨基酸与衍生自胸苷序列的β-氨基酸成分交替，以三链体模式特异性识别并结合脱氧和核糖寡腺苷酸。
• Synthesis of aminodisaccharide–nucleoside conjugates for RNA binding
  作者：Li Cai、Qin Li、Bo Ren、Zhen-Jun Yang、Liang-Ren Zhang、Li-He Zhang

  DOI：10.1016/j.tet.2007.06.002

  日期：2007.8

  Two types of aminodisaccharide-nucleoside conjugates were synthesized by the condensation of azidodisaccharide and nucleoside using aliphatic diamine as a linker. The corresponding azidodisaccharides could be yielded from neamine in good yield. The binding properties to 16S RNA of these conjugates were evaluated by SPR. It was found that the nucleobase played a significant role in the binding of these conjugates to 16S RNA and a shorter linker between the aminodisaccharide and nucleoside was favorable for 16S RNA binding. (c) 2007 Elsevier Ltd. All rights reserved.
• Synthesis of DNA analogues with novel carboxamidomethyl phosphonamide and glycinamide internucleoside linkages
  作者：V.A. Efimov、A.A. Buryakova、O.G. Chakhmakhcheva

  DOI：10.1016/s0960-894x(98)00153-x

  日期：1998.5

  Thymidine oligonucleotide analogues with phosphodiester bonds fully substituted by carboxamidomethyl phosphonamide, or glycinamide linkages were synthesized on a solid support, and their hybridization properties toward DNA and RNA targets were determined by Tm analysis. (C) 1998 Elsevier Science Ltd. All rights reserved.