phenoxyacetyl-1-O-benzotriazolide | 375345-66-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: phenoxyacetyl-1-O-benzotriazolide
• 英文别名: hydroxybenzotriazolyl acetate；benzotriazol-1-yl 2-phenoxyacetate
• CAS: 375345-66-7
• 化学式: C₁₄H₁₁N₃O₃
• 分子量: 269.26
• InChiKey: UIBSSAQKQZDACX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.47
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  66.24
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  phenoxyacetyl-1-O-benzotriazolide 在 吡啶 、 potassium phosphate 、 三甲基氯硅烷 作用下， 反应 40.0h， 生成 N2-phenoxyacetyl-5'-O-(4,4'-dimethoxytrityl)guanosine
  参考文献：
  名称：

  High yield protection of purine ribonucleosides for phosphoramidite RNA synthesis

  摘要：

  We report high yield procedures for protection of purine ribonucleosides based on a reaction which allows concomitant highly regiospecific 2'-silylation and 3'-phosphitylation. Subsequent cleavage of the H-phosphonate monoester moiety without silyl migration provides intermediates ready for phosphitylation by standard methods to give fully protected phosphoramidites. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00733-9
• 作为产物：
  描述：

  1-羟基苯并三唑 、 苯氧乙酰氯 以 乙腈 为溶剂， 生成 phenoxyacetyl-1-O-benzotriazolide
  参考文献：
  名称：

  Proofing of Photolithographic DNA Synthesis with 3‘,5‘-Dimethoxybenzoinyloxycarbonyl-Protected Deoxynucleoside Phosphoramidites

  摘要：

  We have evaluated in a microchip format the photochemical solid-phase phosphoramidite DNA synthesis method we previously developed. A set of nucleoside building blocks with "easy-off" base protecting groups was prepared bearing photolabile 5'-O-dimethoxybenzoincarbonate (DMBOC) groups. Photolysis rates and cycle yields for these DMBOC-protected nucleotides covalently attached to planar, derivatized glass surfaces were determined by fluorescence imaging-based methods earlier developed by McGall et al. and described in detail elsewhere. Data were obtained for both 280/310 and 365/400 nm irradiation in a range of solvents. Deprotection of the DMBOC occurs fastest in a nonpolar medium or without solvent. The coupling efficiency of these amidites in the synthesis of homopolymers was determined to be in the range 80-97%, with purines generally showing lower efficiency than pyrimidines. These DMBOC-protected monomers were used to prepare a 4 x 4 array of 16 decanucleotides of the sequence 5'-AAXTAXCTAC-chip, where X = A, C, G, or T. The array was hybridized with a target deoxyeicosanucleotide of the sequence fluorescein-5'-CTGAACG-GTAGCATCTTGAC. Surface fluorescence imaging demonstrated sequence-specific hybridization to this probe.

  DOI：

  10.1021/jo970872s

文献信息

• Synthesis of DNA Templates Containing the Fifth Base, 2-Amino-6-(dimethylamino)purine, for Specific Transcription Involving Unnatural Base Pairs
  作者：Ichiro Hirao、Takahiko Nojima、Tsuneo Mitsui、Shigeyuki Yokoyama

  DOI：10.1246/cl.2001.914

  日期：2001.9

  An unnatural nucleobase, pyridin-2-one (denoted as y), can be specifically incorporated into RNA opposite 2-amino-6-(dimethylamino)purine (denoted as x) in DNA templates by T7 RNA polymerase. For the easy preparation of DNA templates containing x, protecting groups for the 2-amino group of x were examined. Although the general N2 protecting groups, such as isobutyryl and acetyl, resisted removal by the usual treatment with concentrated ammonia at 55 °C for 6 h, the N2-phenoxyacetyl group was successfully removed from the protected oligomers. This DNA synthesis would be a useful method for preparation of DNA templates toward enzymatic incorporation of unnatural nucleosides into RNA at desired positions.

  一种非天然核碱基吡啶-2-酮（以 y 表示）可通过 T7 RNA 聚合酶特异性地与 DNA 模板中的 2-氨基-6-(二甲基氨基)嘌呤（以 x 表示）相对结合到 RNA 中。为了便于制备含有 x 的 DNA 模板，研究人员对 x 的 2-氨基保护基团进行了研究。虽然一般的 N2 保护基（如异丁酰基和乙酰基）在 55 ℃ 下用浓氨水处理 6 小时后不能去除，但 N2-苯氧基乙酰基却能成功地从受保护的低聚物中去除。这种 DNA 合成方法是一种有用的 DNA 模板制备方法，可用于在所需位置将非天然核苷通过酶结合到 RNA 中。