5'-Dimethoxytrityl-2'-deoxyuridine-5-propionamide | 96203-41-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 5'-Dimethoxytrityl-2'-deoxyuridine-5-propionamide
• 英文别名: 5-<3-<(2-aminoethyl)amino>-3-oxopropyl>-5'-O-DMT-2'-deoxyuridine；5'-O-DMT-5-<3-<(2-aminoethyl)-amino>-3-oxopropyl>-2'-deoxyuridine；5'-O-[4,4'-dimethoxytrityl]-5-[3-[(2-aminoethyl)amino]-3-oxopropyl]-2'-deoxyuridine；N-(2-aminoethyl)-3-[1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxyoxolan-2-yl]-2,4-dioxopyrimidin-5-yl]propanamide
• CAS: 96203-41-7
• 化学式: C₃₅H₄₀N₄O₈
• 分子量: 644.725
• InChiKey: MVPHUCAAIQDARH-XAGDYJCDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.22
• 重原子数：
  47.0
• 可旋转键数：
  14.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  167.13
• 氢给体数：
  4.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  5'-Dimethoxytrityl-2'-deoxyuridine-5-propionamide 在 盐酸 、 二乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 18.25h， 生成 5-<3-<<2-<<2-Amino-3-(1H-imidazol-4-yl)-1-oxopropyl>amino>ethyl>amino>-3-oxopropyl>-2'-deoxyuridine
  参考文献：
  名称：

  Synthesis and characterization of nucleoside peptides: toward chemical ribonucleases. 1

  摘要：

  DOI：

  10.1021/jo00304a026
• 作为产物：
  描述：

  5'-O-[4,4'-dimethoxytrityl]-5-[3-methoxy-3-oxopropyl]-2'-deoxyuridine 、 乙二胺 生成 5'-Dimethoxytrityl-2'-deoxyuridine-5-propionamide
  参考文献：
  名称：

  新的核酸光亲和探针的开发：4-硫代胸腺嘧啶核苷标记的核苷类似物的合成

  摘要：

  已经构建了新的核酸光亲和探针1a，1b，2和3，其中在脱氧尿苷的C-5位引入的可变链的末端连接有4-硫代胸腺嘧啶。

  DOI：

  10.1016/s0040-4039(00)75986-7

文献信息

• Toward Chemical Ribonucleases. 2. Synthesis and Characterization of Nucleoside-Bipyridine Conjugates. Hydrolytic Cleavage of RNA by Their Copper(II) Complexes
  作者：Amil Modak、Janice Gard、Michael Merriman、Kimberly Winkeler、James Bashkin、Michael Stern

  DOI：10.1021/ja00001a041

  日期：1991.1

  As part of our program to develop chemical ribonucleases that cleave RNA by phosphodiester hydrolysis, a systematic study of covalently linked nucleoside-2,2'-bipyridine (bpy) conjugates is described

  作为我们开发通过磷酸二酯水解切割 RNA 的化学核糖核酸酶的计划的一部分，描述了对共价连接的核苷-2,2'-联吡啶 (bpy) 偶联物​​的系统研究
• Synthesis of 4-Thiothymine Based Photolabels as New Tools for Nucleic Acids Structural Studies in Solution: Formation of Long-Range Photo-Cross-Links within a Hammerhead Ribozyme Domain
  作者：Carole Saintomé、Pascale Clivio、Jean-Louis Fourrey、Anne Woisard、Philippe Laugâa、Alain Favre

  DOI：10.1016/s0040-4020(00)00024-7

  日期：2000.2

  The nucleosidic photolabels 2–5, able to form long-range photo-cross-links, have been used to further investigate the tertiary folding of a hammerhead ribozyme domain. These photolabels derive from 2′-deoxyuridine which is substituted at its C-5 position with a photoactivable 4-thiothymine unit linked by a chain of various length and rigidity. Derivatives 2–5 were inserted at strategic positions of

  所述核苷photolabels 2 - 5，能够形成远距离光交联，已经使用以进一步调查锤头状核酶结构域的三级折叠。这些光标记物衍生自2'-脱氧尿苷，其在其C-5位置被可光活化的4-硫代胸腺嘧啶单元取代，该单元通过各种长度和刚性的链连接。衍生物2 - 5分别以deoxysubstrate类似物（的战略位置插入德尚锤头状核酶（的）RZ）。共价交联是通过在裂解条件下组装的Rz - dS络合物的366 nm辐照产生的。该保证金不映射涉及这些交联的残基以给出新的邻近数据集，扩展了先前通过使用2'-deoxy-4-thiouridine 1进行固有光标记获得的那些。因此，与零长交联剂1，photolabels 2 - 5显示出其严重依赖于接头的长度和柔性和其掺入的位点较高的勘探容量。有趣的是，与1相反，这些光标记物能够交联涉及双G的残基：错配以及相邻碱基对的残基。这些发现表明错配结构域在溶液中表现出意想不到的构象灵活性。
• Synthesis and characterization of DNA oligomers and duplexes containing covalently attached molecular labels: comparison of biotin, fluorescein, and pyrene labels by thermodynamic and optical spectroscopic measurements
  作者：Joshua Telser、Kenneth A. Cruickshank、Larry E. Morrison、Thomas L. Netzel

  DOI：10.1021/ja00200a011

  日期：1989.8

  Synthese de nucleotides modifies, de la cytidine et de l'uridine, permettant la liaison avec des composes fluorescents tel que la biotine, le pyrenebutyrate-1, la fluorescesine, afin de rendre fluorescent des oligonucleotides

  Synthese de nucleotides modates, de la cytidine et de l'uridine, permettant la liaison avec des composesfluores tel que la biotine, le pyrenebutyrate-1, la fluorescesine, afin de rendrefluorescence des oligonucleotides
• Sondhi; Xie; Modak, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1998, vol. 37, # 11, p. 1097 - 1103
  作者：Sondhi、Xie、Modak、Bashkin

  DOI：——

  日期：——
• Synthesis and characterization of oligonucleotide peptides
  作者：James K. Bashkin、Randy J. McBeath、Anil S. Modak、Kirby R. Sample、William B. Wise

  DOI：10.1021/jo00009a044

  日期：1991.4

  The transport and reactivity of oligonucleotides may be altered by attaching pendant peptides, and it is of interest to develop general synthetic methods for such bioconjugates. Two protecting group strategies are described for the synthesis of nucleotide peptides containing a lysine residue. The preparation of a lysine-nucleopeptide phosphoramidite reagent is described, along with its use in solid-phase DNA synthesis. Di- and trinucleotides were prepared with pendant and extensively characterized by NMR. These studies showed the peptide side chains to have survived DNA synthesis conditions; we then incorporated nucleopeptide residues into longer oligonucleotides. A similar approach is described for the preparation of oligonucleotide histidines. Previously reported histidine-nucleopeptides serve as precursors to phosphoramidites and to phosphodiester DNA building blocks. Both solution- and solid-phase techniques are presented for the preparation of histidine-containing oligonucleotides. The methodology developed here allows the incorporation of nucleopeptide residues at internal positions in a DNA sequence, using standard reagents. We present a complete description of the synthesis, purification, and characterization (via mass spectral and NMR methods) of the novel compounds.