dNaM | 1117893-19-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dNaM
• 英文别名: 2-(2-Deoxy-beta-D-ribofuranosyl)-3-methoxynaphthalene；(2R,3S,5R)-2-(hydroxymethyl)-5-(3-methoxynaphthalen-2-yl)oxolan-3-ol
• CAS: 1117893-19-2
• 化学式: C₁₆H₁₈O₄
• 分子量: 274.317
• InChiKey: XVSHFDVHYNHNDU-NUEKZKHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dNaM 在 磷酸三甲酯 、 1,8-双二甲氨基萘 、 N,N'-二环己基碳二亚胺 、 三氯氧磷 作用下， 以 水 、 二甲基亚砜 、 叔丁醇 为溶剂， 反应 80.5h， 生成
  参考文献：
  名称：

  Chemical Stabilization of Unnatural Nucleotide Triphosphates for the in Vivo Expansion of the Genetic Alphabet

  摘要：

  We have developed an unnatural base pair (UBP) and a semisynthetic organism (SSO) that imports the constituent unnatural nucleoside triphosphates and uses them to replicate DNA containing the UBP. However, propagation of the UBP is at least in part limited by the stability of the unnatural triphosphates, which are degraded by cellular and secreted phosphatases. To circumvent this problem, we now report the synthesis and evaluation of unnatural triphosphates with their beta, gamma-bridging oxygen replaced with a difluoromethylene moiety, yielding dNaMTP(CF2) and dTPT3TP(CF2). We find that although dNaMTP(CF2) cannot support in vivo replication, likely due to poor polymerase recognition, dTPT3TP(CF2) can, and moreover, its increased stability can contribute to increased UBP retention. The data demonstrate the promise of this chemical approach to SSO optimization, and suggest that other modifications should be sought that confer phosphatase resistance without interfering with polymerase recognition.

  DOI：

  10.1021/jacs.6b12731
• 作为产物：
  描述：

  在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 dNaM
  参考文献：
  名称：

  Seo, Young Jun; Hwang, Gil Tae; Ordoukhanian, Phillip, Journal of the American Chemical Society, 2009, vol. 131, p. 3246 - 3252

  摘要：

  DOI：

文献信息

• 非天然碱基核苷酸磷酸单酯类前药分子及其制备方法和应用
  申请人：河南师范大学

  公开号：CN114249788B

  公开（公告）日：2023-08-08

  本发明公开了一种非天然碱基核苷酸磷酸单酯类前药分子及其制备方法和应用，非天然碱基核苷酸磷酸单酯类前药分子的具体结构如下：其中R为本发明还具体公开了该非天然碱基核苷酸磷酸单酯类前药分子的合成方法及其在制备抗肿瘤细胞活性药物中的应用。本发明的非天然碱基核苷酸磷酸单酯类前药分子合成方法简单、收率较高、节约成本，并且具有良好的跨膜效率，其跨膜效率是非天然碱基核苷酸的8‑10倍，同时对MCF‑7细胞、A375细胞、Hela细胞或HepG2癌细胞具有一定的抑制作用。
• Major Groove Substituents and Polymerase Recognition of a Class of Predominantly Hydrophobic Unnatural Base Pairs
  作者：Thomas Lavergne、Denis A. Malyshev、Floyd E. Romesberg

  DOI：10.1002/chem.201102066

  日期：2012.1.23

  different substituents designed to be oriented into the developing major groove and an analysis of their insertion opposite d5SICS by Kf and Thermus aquaticus DNA polymerase I (Taq). We also expand the analysis of the previously optimized pair, dNaM–d5SICS, to include replication by Taq. Finally, the efficiency and fidelity of PCR amplification of the base pairs by Taq or Deep Vent polymerases was examined

  用非自然碱基对扩展遗传字母表是合成生物学的长期目标。我们已经开发了一类非天然型碱基对，d之间形成5SICS和d的类似物mmO2公司由Klenow片段（KF）DNA聚合酶有效且选择性复制。为了进一步表征和优化复制，我们报告了五种新的 d MMO2类似物的合成，这些类似物带有不同的取代基，设计用于定向到发育中的大沟，并通过 Kf 和水生栖热菌DNA 聚合酶 I分析它们在 d 5SICS对面的插入。塔克）。我们还扩展了对先前优化的对 d NaM –d 5SICS 的分析, 包括 Taq 的复制。最后，检查了 Taq 或 Deep Vent 聚合酶对碱基对进行 PCR 扩增的效率和保真度。由此产生的构效关系数据表明，有效复制的主要决定因素是最小化去溶剂化效应和引入有利的疏水堆积，并且 Taq 比 Kf 对结构变化更敏感。此外，我们确定了模拟（d NMO1）是用于d更好的合作伙伴5SICS比任何先前
• NUCLEIC ACID SYNTHESIS USING DNA POLYMERASE THETA
  申请人：Molecular Assemblies, Inc.

  公开号：US20180274001A1

  公开（公告）日：2018-09-27

  Provided herein are methods for template-independent synthesis of oligonucleotides using a DNA polymerase. Also provided are methods for template-directed synthesis of oligonucleotides and for sequencing of nucleic acids using DNA polymerase theta and 3′-aminoalkoxy nucleotides.
• Seo, Young Jun; Hwang, Gil Tae; Ordoukhanian, Phillip, Journal of the American Chemical Society, 2009, vol. 131, p. 3246 - 3252
  作者：Seo, Young Jun、Hwang, Gil Tae、Ordoukhanian, Phillip、Romesberg, Floyd E.

  DOI：——

  日期：——
• Chemical Stabilization of Unnatural Nucleotide Triphosphates for the in Vivo Expansion of the Genetic Alphabet
  作者：Aaron W. Feldman、Vivian T. Dien、Floyd E. Romesberg

  DOI：10.1021/jacs.6b12731

  日期：2017.2.15

  We have developed an unnatural base pair (UBP) and a semisynthetic organism (SSO) that imports the constituent unnatural nucleoside triphosphates and uses them to replicate DNA containing the UBP. However, propagation of the UBP is at least in part limited by the stability of the unnatural triphosphates, which are degraded by cellular and secreted phosphatases. To circumvent this problem, we now report the synthesis and evaluation of unnatural triphosphates with their beta, gamma-bridging oxygen replaced with a difluoromethylene moiety, yielding dNaMTP(CF2) and dTPT3TP(CF2). We find that although dNaMTP(CF2) cannot support in vivo replication, likely due to poor polymerase recognition, dTPT3TP(CF2) can, and moreover, its increased stability can contribute to increased UBP retention. The data demonstrate the promise of this chemical approach to SSO optimization, and suggest that other modifications should be sought that confer phosphatase resistance without interfering with polymerase recognition.