3'-O-benzoyl-thymidine 5'-<(2-cyanoethyl)-N,N'-diisopropyl> phosphoramidite | 249286-78-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 3'-O-benzoyl-thymidine 5'-<(2-cyanoethyl)-N,N'-diisopropyl> phosphoramidite
• 英文别名: 3'-O-benzoylthymidine-5'-O-(2-cyanoethyl N,N-diisopropylphosphoramidite)；Bz(-3)[N(iPr)2P(OCH2CH2CN)(-5)]2-deoxy-D-eryPenf(b)-thymin-1-yl；[(2R,3S,5R)-2-[[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] benzoate
• CAS: 249286-78-0
• 化学式: C₂₆H₃₅N₄O₇P
• 分子量: 546.56
• InChiKey: WUDLPHFAXAAHHM-FDXOTVGBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  38
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  130
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3'-O-benzoyl-thymidine 5'-<(2-cyanoethyl)-N,N'-diisopropyl> phosphoramidite 在 四氮唑 、 苯基二硫化物 作用下， 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Nucleotide libraries as a source of biologically relevant chemical diversity: solution-phase synthesis

  摘要：

  Solution-phase parallel synthesis of nucleotide library I consisting of 150 members is reported. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00210-9
• 作为产物：
  描述：

  2-氰乙基N,N-二异丙基氯亚磷酰胺 、 3'-O-benzoyl-5'-O-p-toluenesulfonyl-thymidine 在 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以81%的产率得到3'-O-benzoyl-thymidine 5'-<(2-cyanoethyl)-N,N'-diisopropyl> phosphoramidite
  参考文献：
  名称：

  Syntheses of inhibitors for the enzyme thymidine 5′-diphosphate-glucose-4,6-dehydratase (EC 4.2.1.46)

  摘要：

  Inhibitors of the enzyme thymidine 5'-diphosphate-glucose-4,6-dehydratase (EC 4.2.1.46) were synthesised starting from thymidine, 2-deoxy-uridine and -cytidine. The diphosphate moieties have either been replaced by methylene diphosphonate or phosphoryl hydroxyacetic acid to yield inhibitors in a similar range to thymidine 5'-diphosphate itself. Spacers were attached to various positions, of which those at C-5 of the nucleobase were suitable analogues and showed a mixed type of inhibition characteristics, whereas attachment at other sites led to marginally active or inactive inhibitors. These investigations will prepare the ground for developing a purification procedure based on affinity chromatography. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00074-9

文献信息

• Synthesis and Properties of Aminoacylamido-AMP:  Chemical Optimization for the Construction of an <i>N</i>-Acyl Phosphoramidate Linkage
  作者：Tomohisa Moriguchi、Terukazu Yanagi、Masao Kunimori、Takeshi Wada、Mitsuo Sekine

  DOI：10.1021/jo0008338

  日期：2000.12.1

  This paper describes the design and synthesis of a new type of aminoacyl-adenylate analogue (aa-AMPN) having an N-acyl phosphoramidate linkage where the oxygen atom of the mixed anhydride bond of aminoacyl-adenylate (aa-AMP) is replaced by an amino group. This new type of aa-AMP analogue is expected to be useful as material for studies on the recognition mechanism of the aminoacylation of tRNA and

  本文介绍了具有N-酰基氨基磷酸酯键的新型氨基酰基-腺苷酸类似物（aa-AMPN）的设计和合成，其中氨基酰基-腺苷酸（aa-AMP）的混合酸酐键的氧原子被氨基。这种新型的aa-AMP类似物有望用作研究tRNA氨基酰化和其他生化反应识别机制的材料。羧酰胺的亚磷酰胺衍生物与核苷衍生物的缩合失败，因为活化的亚磷酰胺衍生物不仅与羟基反应，而且与另一种反应性物质反应。通过5'-O-亚磷酰胺基腺苷衍生物与羧酰胺衍生物的反应研究了另一种方法。选择TBTr和TSE基团分别用于保护氨基酸酰胺的氨基和磷酸基。详细研究表明，使用5-（3,5-二硝基苯基）-1H-四唑作为亚磷酰胺的活化催化剂可在10分钟内迅速缩合，从而得到完全保护的aa-AMPN衍生物。没有发生副反应。通过两步程序对这些产物进行脱保护，得到高产率的aa-AMPN衍生物。还证明由此获得的aa-AMPN在酸性和碱性条件下均是稳定的，例如0.1M HCl（pH