N-trifluoroacetyl-1-amino-5-hexyne | 149798-22-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-trifluoroacetyl-1-amino-5-hexyne
• 英文别名: 6-trifluoroacetamido-1-hexyne；2,2,2-trifluoro-N-hex-5-ynylacetamide
• CAS: 149798-22-1
• 化学式: C₈H₁₀F₃NO
• 分子量: 193.169
• InChiKey: KDKMWGKBDBWRPF-UHFFFAOYSA-N

物化性质

• 沸点：
  239.4±40.0 °C(Predicted)
• 密度：
  1.158±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-trifluoroacetyl-1-amino-5-hexyne 在 palladium on activated charcoal 吡啶 、 copper(l) iodide 、 四(三苯基膦)钯 、 氢气 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 反应 42.0h， 生成 5-(6-N-(trifluoroacetyl)aminohexyl)-4-N-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxycytidine 2-cyanoethyl N,N-diisopropylphosphoramidite
  参考文献：
  名称：

  Zwitterionic DNA

  摘要：

  As a strategy to make DNA net charge neutral, oligodeoxynucleotides bearing pyrimidine 5-omega-aminohexyl substituents have been synthesized and characterized. The resultant zwitterionic oligomers bind to natural DNA at low ionic strength as well or better than does natural DNA with itself, even when all of the nucleotides in a given single. strand are rendered zwitterionic. As would be expected, stabilities of duplexes bearing zwitterionic strands are relatively insensitive to changes in solution ionic strength as compared with natural DNA. Somewhat surprising, however, is the finding that a DNA duplex composed of a fully zwitterionic strand and a natural complementary strand exhibits no change in stability over a 20-fold change in ionic strength. Thus, double- and single-stranded states in this case have equivalent charge densities, consistent with the zwitterionic strand contributing no net charge. Stabilization due to the ammonium ions was verified by comparing free energies of DNA duplexes bearing hexyl tethered ammonium ions with those bearing simply hexyl groups devoid of ammonium ions. This comparison showed that without an added positive ammonium ion, the hexyl tether itself has a severe and cumulative unfavorable effect on duplex stability. Finally, zwitterionic nucleotides are found to distinguish matched from mismatched nucleotides in complementary DNA strands to a degree that rivals natural DNA.

  DOI：

  10.1021/ja00069a009
• 作为产物：
  描述：

  5-己炔-1-胺 、 三氟乙酸乙酯 以 甲醇 为溶剂， 反应 17.0h， 以60%的产率得到N-trifluoroacetyl-1-amino-5-hexyne
  参考文献：
  名称：

  C8-炔基-和烷基氨基取代的2'-脱氧鸟苷：核酸修饰的通用接头

  摘要：

  修饰的核苷与柔性通用接头的结合对于核酸的合成后修饰具有巨大的价值。因此，首次合成了C8-炔基-和烷基氨基取代的2'-脱氧鸟苷，并将其掺入短的寡核苷酸序列中。讨论了这些C8取代的2'-脱氧鸟苷的顺式构象的偏爱性和双链体的稳定性。还检查了Z-DNA的稳定作用。

  DOI：

  10.1016/j.tet.2008.01.091

文献信息

• Antisense oligonucleotides comprising 5-aminoalkyl pyrimidine nucleotides
  申请人：The Regents of the University of California

  公开号：US05596091A1

  公开（公告）日：1997-01-21

  Replacement of the natural nucleotides with unnatural zwitterionic nucleotides having a cationic moiety tethered to the base (or analog thereof) results in oligodeoxynucleotides with diminished charge but undiminished ability to complex with DNA at low ionic strengths. We have now discovered that DNA can be made fully zwitterionic by introducing tethered cationic moieties to the bases without affecting duplex formation. The resulting oligonucleotides have the further advantages of being nuclease resistant.

  将天然核苷酸替换为带有阳离子基团的非天然带电核苷酸（或其类似物）会导致寡脱氧核苷酸带有减少的电荷，但在低离子强度下与DNA结合的能力不减。我们现在发现，通过向碱基引入带有连接的阳离子基团，可以使DNA完全成为带电核酸，而不影响双链形成。由此产生的寡核苷酸具有耐核酸酶的额外优势。
• 3'-Deoxyribonucleotide derivatives
  申请人：The Institute of Physical and Chemical Research

  公开号：US06265569B1

  公开（公告）日：2001-07-24

  Disclosed are 3′-deoxyribonucleotide derivatives represented by the following general formula [I]: Q—V—(CH2)n—NH—R  [I] wherein Q represents a 3′-deoxyribonucleotide residue, n represents an integer not less than 4, V represents —C≡C— or —CH═CH—, and R represents a fluorescent group. The above 3′-deoxyribonucleotide derivatives are derivatives with improved rates for incorporation using RNA polymerases, which are useful as terminators in the DNA sequence determination methods utilizing RNA polymerases.

  披露了由以下一般公式表示的3′-脱氧核苷酸衍生物：Q—V—(CH2)n—NH—R 其中 Q代表一个3′-脱氧核苷酸残基，n代表不小于4的整数，V代表—C≡C—或—CH═CH—，R代表一个荧光基团。上述3′-脱氧核苷酸衍生物是具有改善RNA聚合酶使用速率的衍生物，可用作DNA序列测定方法中利用RNA聚合酶的终止子。
• Method of DNA sequencing
  申请人：The Institute of Physical and Chemical Research

  公开号：US06365350B1

  公开（公告）日：2002-04-02

  Disclosed are methods for determining DNA nucleotide sequences comprising reacting ribonucleoside 5′-triphosphates and 3′-dNTP derivatives in the presence of an RNA polymerase modified so as to enhance its ability for incorporating the 3′-dNTP derivatives and a DNA fragment containing a promoter sequence for the RNA polymerase to obtain a nucleic acid transcription product, separating the resulting nucleic acid transcription product, and determining a nucleic acid sequence from the resulting separated fraction. These methods can produce a transcription product of a long chain and afford more accurate sequence data where fluctuation of signals from labeled deoxyribonucleotides is reduced.

  揭示了一种确定DNA核苷酸序列的方法，包括在存在已经修改以增强其用于将3′-dNTP衍生物合并的RNA聚合酶的情况下，反应核苷酸5′-三磷酸酯和3′-dNTP衍生物，以及包含用于RNA聚合酶的启动子序列的DNA片段，以获得核酸转录产物，分离所得的核酸转录产物，并从分离的分数中确定核酸序列。这些方法可以产生长链的转录产物，并提供更准确的序列数据，减少了标记的脱氧核糖核苷酸信号波动。
• METHOD OF DNA SEQUENCING
  申请人：THE INSTITUTE OF PHYSICAL & CHEMICAL RESEARCH

  公开号：EP0978569A1

  公开（公告）日：2000-02-09

  A method of DNA sequencing comprising reacting a ribonucleoside 5'-triphosphate with a 3'dNTP derivative in the presence of a mutated RNA polymerase modified so as to enhance the ability to take up the 3'dNTP derivative and a DNA fragment containing a promoter sequence for the RNA polymerase, separating the nucleic acid transcription product thus obtained, and reading the sequence of the nucleic acid from the fraction thus separated. By using this method, a long-chain transcription product can be formed and more accurate sequence data with little change in the signals from labeled deoxyribonucleotides can be obtained.

  一种 DNA 测序方法，包括在经过修饰以提高吸收 3'dNTP 衍生物能力的突变 RNA 聚合酶和含有 RNA 聚合酶启动子序列的 DNA 片段存在的情况下，使核糖核苷 5'- 三磷酸酯与 3'dNTP 衍生物反应，分离由此获得的核酸转录产物，并从由此分离的部分读取核酸序列。使用这种方法可以形成长链转录产物，获得更准确的序列数据，而标记脱氧核苷酸的信号变化很小。
• 3'-DEOXYRIBONUCLEOTIDE DERIVATIVES
  申请人：THE INSTITUTE OF PHYSICAL & CHEMICAL RESEARCH

  公开号：EP1046648A1

  公开（公告）日：2000-10-25

  3'-Deoxyribonucleotide derivatives represented by the following general formula [I]: Q-V-(CH2)n-NR-R wherein Q represents a 3'-deoxyribonucleotide residue; n is an integer of 4 or more; V represents -C≡C- or -CH=CH-; and R represents a fluorescent group. Because of having been improved in the uptake efficiency by RNA polymerases, these derivatives are useful as terminators in DNA base sequencing methods with the use of RNA polymerases.

  由以下通式[I]代表的 3'-脱氧核苷酸衍生物：Q-V-(CH2)n-NR-R 其中 Q 代表 3'-脱氧核苷酸残基；n 是 4 或更多的整数；V 代表 -C≡C- 或 -CH=CH-；R 代表荧光基团。由于提高了 RNA 聚合酶的吸收效率，这些衍生物在使用 RNA 聚合酶的 DNA 碱基测序方法中可用作终止子。