1-(2-amino-5-O-4,4'-dimethoxytrityl-2-N,4-C-methylene-2-N-trifluoroacetyl-β-D-ribofuranosyl)thymine | 219600-96-1

• 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: 1-(2-amino-5-O-4,4'-dimethoxytrityl-2-N,4-C-methylene-2-N-trifluoroacetyl-β-D-ribofuranosyl)thymine
• 英文别名: 1-[(1R,3R,4R,7S)-1-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-7-hydroxy-5-(2,2,2-trifluoroacetyl)-2-oxa-5-azabicyclo[2.2.1]heptan-3-yl]-5-methylpyrimidine-2,4-dione
• CAS: 219600-96-1
• 化学式: C₃₄H₃₂F₃N₃O₈
• 分子量: 667.639
• InChiKey: WBYVGYDJJPTIAL-FDCUTXSFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  48
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  127
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1-(2-amino-5-O-4,4'-dimethoxytrityl-2-N,4-C-methylene-2-N-trifluoroacetyl-β-D-ribofuranosyl)thymine 在 吡啶 、 三乙基硅烷 、 二氯乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 22.5h， 生成 1-(3-O-acetyl-2-amino-2-N,4-C-methylene-2-N-trifluoroacetyl-β-D-ribofuranosyl)thymine
  参考文献：
  名称：

  Enzymatic polymerisation involving 2′-amino-LNA nucleotides

  摘要：

  The triphosphate of the thymine derivative of 2'-amino-LNA (2'-amino-LNA-TTP) was synthesised and found to be a good substrate for Phusion (R) HF DNA polymerase, allowing enzymatic synthesis of modified DNA encoded by an unmodified template. To complement this, 2'-amino-LNA-T phosphoramidites were incorporated into DNA oligonucleotides which were used as templates for enzymatic synthesis of unmodified DNA using either KOD, KOD XL or Phusion polymerases. 2'-Amino-LNA-T in the template and 2'-amino-LNA-TTP as a substrate both decreased reaction rate and yield compared to unmodified DNA, especially for sequences with multiple 2'-amino-LNA-T nucleotides. Crown Copyright (C) 2012 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.03.073
• 作为产物：
  描述：

  1-[(2R,3R,4S,5R)-4-benzyloxy-5-(benzyloxymethyl)-3-hydroxy-5-(hydroxymethyl)tetra-hydrofuran-2-yl]-5-methylpyrimidine-2,4-dione 在 palladium on activated charcoal 4-二甲氨基吡啶 、 ammonium formate 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 反应 39.5h， 生成 1-(2-amino-5-O-4,4'-dimethoxytrityl-2-N,4-C-methylene-2-N-trifluoroacetyl-β-D-ribofuranosyl)thymine
  参考文献：
  名称：

  Synthesis of 2‘-Amino-LNA:  A Novel Conformationally Restricted High-Affinity Oligonucleotide Analogue with a Handle

  摘要：

  DOI：

  10.1021/jo9814445

文献信息

• Functionalized LNA (locked nucleic acid): high-affinity hybridization of oligonucleotides containing N-acylated and N-alkylated 2′-amino-LNA monomers
  作者：Mads D. Sørensen、Michael Petersen、Jesper Wengel

  DOI：10.1039/b307026c

  日期：——

  A molecular dynamics (MD) simulation, synthesis and very efficient hybridization for a series of N-acylated and N-alkylated derivatives of 2′-amino-LNA are reported.

  报道了一系列N-酰化和N-烷基化的2′-氨基-LNA衍生物的分子动力学（MD）模拟、合成及非常高效的杂交。
• Optimized DNA targeting using N,N-bis(2-pyridylmethyl)-β-alanyl 2′-amino-LNA
  作者：B. Ravindra Babu、Patrick J. Hrdlicka、Christine J. McKenzie、Jesper Wengel

  DOI：10.1039/b417101b

  日期：——

  Incorporation of N,N-bis(2-pyridylmethyl)-β-alanyl 2′-amino-LNA (bipyridyl-functionalized 2′-amino locked nucleic acid) monomers into DNA strands enables high-affinity targeting of complementary DNA with excellent Watson–Crick selectivity in the presence of divalent metal ions. Positioning of bipyridyl-functionalized 2′-amino-LNA monomers in two complementary DNA strands in a “3′-end zipper” constitution allows modulation of duplex stability, i.e., a strong stabilizing effect with one equivalent of divalent metal ion per bipyridyl pair, or a strong destabilizing effect with an excess of divalent metal ions.

  将N,N-双（2-吡啶基甲基）-δ-丙氨酰2â²-氨基-LNA（双吡啶基官能化2â²-氨基锁定核酸）单体掺入DNA链中，可实现互补DNA的高亲和性靶向，在二价金属离子存在下具有出色的WatsonâCrick选择性。将双吡啶基官能化的 2â²-氨基-LNA单体以 "3â²-末端拉链 "的结构置于两条互补DNA链中，可以调节双链的稳定性，即每对双吡啶基含有一个等量的二价金属离子时，会产生强烈的稳定作用；而二价金属离子过量时，则会产生强烈的失稳作用。
• Parallel synthesis of oligonucleotides containing <i>N</i>-acyl amino-LNA and their therapeutic effects as anti-microRNAs
  作者：Tomo Takegawa-Araki、Kai Yasukawa、Norihiko Iwazaki、Hideto Maruyama、Hiroyuki Furukawa、Hiroaki Sawamoto、Satoshi Obika

  DOI：10.1039/d2ob01809h

  日期：——

  (ALNA), maintains excellent duplex stability, and the nitrogen at the 2′-position is an attractive scaffold for functionalization. Herein, a facile and efficient method for the synthesis of various 2′-N-acyl amino-LNA derivatives by direct acylation of the 2′-amino moiety contained in the synthesized oligonucleotides and its fundamental properties are described. The introduction of the acylated amino-LNA

  2'-氨基锁核酸 (ALNA)，保持出色的双链体稳定性，2'-位置的氮是功能化的有吸引力的支架。在此，描述了通过直接酰化合成的寡核苷酸中包含的 2'-氨基部分来合成各种 2' - N-酰基氨基-LNA 衍生物的简便有效的方法及其基本特性。酰化氨基-LNA 的引入增强了分子作为治疗性抗 microRNA 寡核苷酸的效力。
• Enzymatic polymerisation involving 2′-amino-LNA nucleotides
  作者：Marie W. Johannsen、Rakesh N. Veedu、Andreas Stahl Madsen、Jesper Wengel

  DOI：10.1016/j.bmcl.2012.03.073

  日期：2012.5

  The triphosphate of the thymine derivative of 2'-amino-LNA (2'-amino-LNA-TTP) was synthesised and found to be a good substrate for Phusion (R) HF DNA polymerase, allowing enzymatic synthesis of modified DNA encoded by an unmodified template. To complement this, 2'-amino-LNA-T phosphoramidites were incorporated into DNA oligonucleotides which were used as templates for enzymatic synthesis of unmodified DNA using either KOD, KOD XL or Phusion polymerases. 2'-Amino-LNA-T in the template and 2'-amino-LNA-TTP as a substrate both decreased reaction rate and yield compared to unmodified DNA, especially for sequences with multiple 2'-amino-LNA-T nucleotides. Crown Copyright (C) 2012 Published by Elsevier Ltd. All rights reserved.
• Synthesis of 2‘-Amino-LNA:  A Novel Conformationally Restricted High-Affinity Oligonucleotide Analogue with a Handle
  作者：Sanjay K. Singh、Ravindra Kumar、Jesper Wengel

  DOI：10.1021/jo9814445

  日期：1998.12.1