5-N-(6-aminohexyl)carbamoyl-methyl-2'-deoxyuridine 5'-triphosphate

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷酸
• 英文名称: 5-N-(6-aminohexyl)carbamoyl-methyl-2'-deoxyuridine 5'-triphosphate
• 英文别名: 5-(6-aminohexyl)carbamoylmethyl-2'-deoxyuridine-5'-triphosphate；alpha-(6-Aminohexylcarbamoyl)thymidine 5'-triphosphoric acid；[[(2R,3S,5R)-5-[5-[2-(6-aminohexylamino)-2-oxoethyl]-2,4-dioxopyrimidin-1-yl]-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate
• 化学式: C₁₇H₃₁N₄O₁₅P₃
• 分子量: 624.372
• InChiKey: DFCSTSJZPFEWMB-GZBFAFLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -7.7
• 重原子数：
  39
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  294
• 氢给体数：
  8
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  5-N-(6-aminohexyl)carbamoyl-methyl-2'-deoxyuridine 5'-triphosphate 在 ammonium hydroxide 作用下， 以 phosphate buffer 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 5-N-(6-[aminohexyl]aminohexyl)carbamoylmethyl-2'-deoxyuridine 5'-triphosphate
  参考文献：
  名称：

  扩展了使用KOD Dash DNA聚合酶通过PCR制备的修饰DNA的库。

  摘要：

  制备了通过氨基连接臂在C5位带有各种官能团的胸苷类似物，并检测了使用嗜热KOD Dash DNA聚合酶进行PCR的底物活性。该酶接受在C5位带有吡啶，咪唑，生物素，阳离子带电的胍盐，阳离子带电的氨基，巯基吡啶基和菲咯啉基团的胸苷类似物，形成相应的PCR产物。然而，在C5位带有羧基的胸苷类似物是较差的底物，无法获得相应的PCR产物。带有巯基的胸苷类似物也是该酶的不良底物，因为它在PCR条件下通过二硫键二聚。该酶几乎不接受带有负电荷的羧基或大体积基团的胸苷类似物作为底物。KOD Dash DNA聚合酶具有比其他任何DNA聚合酶都要宽的底物特异性，它将扩展可通过PCR制备的修饰DNA的种类。

  DOI：

  10.1039/b504330a

文献信息

• Enzymatic synthesis of labeled DNA by PCR using new fluorescent thymidine nucleotide analogue and superthermophilic KOD dash DNA polymerase
  作者：Tsutomu Obayashi、Mohammed M. Masud、Akiko N. Ozaki、Hiroaki Ozaki、Masayasu Kuwahara、Hiroaki Sawai

  DOI：10.1016/s0960-894x(02)00111-7

  日期：2002.4

  Triphosphate of a new fluorescent labeled thymidine analogue was incorporated as a substrate for PCR using KOD Dash DNA polymerase forming the corresponding fluorescent labeled DNA which is useful for a DNA probe.

  使用KOD Dash DNA聚合酶将新的荧光标记的胸苷类似物的三磷酸酯掺入PCR，作为底物，形成可用于DNA探针的相应的荧光标记的DNA。
• Direct PCR amplification of various modified DNAs having amino acids: Convenient preparation of DNA libraries with high-potential activities for in vitro selection
  作者：Masayasu Kuwahara、Kazuo Hanawa、Kazuomi Ohsawa、Rina Kitagata、Hiroaki Ozaki、Hiroaki Sawai

  DOI：10.1016/j.bmc.2005.11.030

  日期：2006.4

  We synthesized modified 2'-deoxyuridine triphosphates bearing amino acids at the C5 position and investigated their substrate properties for KOD Dash DNA polymerase during polymerase chain reaction (PCR). PCR using C5-modified dUTP having an amino acyl group (arginyl, histidyl, lysyl, phenylalanyl, tryptophanyl, leucyl, prolyl, glutaminyl, seryl, O-benzyl seryl or threonyl group) gave the corresponding full-length PCR products in good yield. Although dUTP analogues bearing aspartyl, glutamyl or cysteinyl were found to be poor substrates for PCR catalyzed by KOD Dash DNA polymerase, optimization of the reaction conditions resulted in substantial generation of full-length product. In the case of reaction using dUTP analogue having a cysteinyl group, addition of a reducing agent improved the reaction yield. Thus, PCRs using KOD Dash DNA polymerase together with amino acyl dUTP provide convenient and efficient preparation of various modified DNA libraries with potential protein-like activities. (c) 2005 Elsevier Ltd. All rights reserved.
• Chemico-enzymatic synthesis of a new fluorescent-labeled DNA by PCR with a thymidine nucleotide analogue bearing an acridone derivative
  作者：Atsushi Shoji、Tomoya Hasegawa、Masayasu Kuwahara、Hiroaki Ozaki、Hiroaki Sawai

  DOI：10.1016/j.bmcl.2006.10.072

  日期：2007.2

  Triphosphate of a thymidine analogue bearing acridone was prepared and incorporated as a substrate for P using KOD Dash DNA polymerase forming a new fluorescent-labeled DNA that is useful as a DNA probe. (c) 2006 Elsevier Ltd. All rights reserved.
• Nucleic Acid with Guanidinium Modification Exhibits Efficient Cellular Uptake
  作者：Tatsuo Ohmichi、Masayasu Kuwahara、Naoko Sasaki、Masatoshi Hasegawa、Takahito Nishikata、Hiroaki Sawai、Naoki Sugimoto

  DOI：10.1002/anie.200500904

  日期：2005.10.21
• Expansion of repertoire of modified DNAs prepared by PCR using KOD Dash DNA polymerase
  作者：Tsutomu Ohbayashi、Masayasu Kuwahara、Masatoshi Hasegawa、Toshiyuki Kasamatsu、Takehiro Tamura、Hiroaki Sawai

  DOI：10.1039/b504330a

  日期：——

  Thymidine analogues bearing a variety of functional groups at the C5-position via an amino-linker arm were prepared and the substrate activity for PCR using thermophilic KOD Dash DNA polymerase was examined. The enzyme accepted the thymidine analogues bearing pyridine, imidazole, biotin, a cationic-charged guanidinium, a cationic-charged amino, mercaptopyridyl and phenanthrolne groups at the C5-position

  制备了通过氨基连接臂在C5位带有各种官能团的胸苷类似物，并检测了使用嗜热KOD Dash DNA聚合酶进行PCR的底物活性。该酶接受在C5位带有吡啶，咪唑，生物素，阳离子带电的胍盐，阳离子带电的氨基，巯基吡啶基和菲咯啉基团的胸苷类似物，形成相应的PCR产物。然而，在C5位带有羧基的胸苷类似物是较差的底物，无法获得相应的PCR产物。带有巯基的胸苷类似物也是该酶的不良底物，因为它在PCR条件下通过二硫键二聚。该酶几乎不接受带有负电荷的羧基或大体积基团的胸苷类似物作为底物。KOD Dash DNA聚合酶具有比其他任何DNA聚合酶都要宽的底物特异性，它将扩展可通过PCR制备的修饰DNA的种类。