DMT-deoxy-2-aminoadenosine | 161786-58-9

• 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: DMT-deoxy-2-aminoadenosine
• CAS: 161786-58-9
• 化学式: C₃₁H₃₂N₆O₅
• 分子量: 568.632
• InChiKey: QIEOPNWKYMXGQE-JIMJEQGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.67
• 重原子数：
  42.0
• 可旋转键数：
  9.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  152.79
• 氢给体数：
  3.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  DMT-deoxy-2-aminoadenosine 在 三甲基氯硅烷 作用下， 反应 0.5h， 生成 5'-O-dimethoxytrityl-N²,N⁶-bis(phenoxyacetyl)-2,6-diaminopurine-2'-deoxyriboside 3'-O-(2-cyanoethyl)-N,N-diisopropylphosphoramidite
  参考文献：
  名称：

  Stabilization of DNA:DNA and DNA:RNA duplexes by substitution of 2′-deoxyadenosine with 2′-deoxy-2-aminoadenosine

  摘要：

  Oligonucleotides containing either 2'-deoxyadenosine d(A) or 2'-deoxy-2-aminoadenosine d(A*) were synthesized and their relative binding affinities to complementary DNA and RNA targets compared. Substitution of dA with dA* resulted in sequence- and target-dependent changes in duplex stability.

  DOI：

  10.1016/s0040-4039(00)77151-6
• 作为产物：
  描述：

  N2-异丁酰-5'-O-(4,4'-二甲氧基三苯基)-2'-脱氧鸟苷 在 ammonium hydroxide 、 氨 、 三氟乙酸酐 作用下， 以 1,4-二氧六环 为溶剂， 反应 72.25h， 生成 DMT-deoxy-2-aminoadenosine
  参考文献：
  名称：

  Stabilization of DNA:DNA and DNA:RNA duplexes by substitution of 2′-deoxyadenosine with 2′-deoxy-2-aminoadenosine

  摘要：

  Oligonucleotides containing either 2'-deoxyadenosine d(A) or 2'-deoxy-2-aminoadenosine d(A*) were synthesized and their relative binding affinities to complementary DNA and RNA targets compared. Substitution of dA with dA* resulted in sequence- and target-dependent changes in duplex stability.

  DOI：

  10.1016/s0040-4039(00)77151-6

文献信息

• Formation of the N2-acetyl-2,6-diaminopurine oligonucleotide impurity caused by acetyl capping
  作者：Andrew A. Rodriguez、Isaiah Cedillo、Brendan P. Mowery、Hans J. Gaus、Seetha S. Krishnamoorthy、Andrew K. McPherson

  DOI：10.1016/j.bmcl.2014.06.025

  日期：2014.8

  The acetyl 'capping' reaction routinely employed during phosphorothioate oligonucleotide synthesis has been implicated in the formation of an impurity species with a mass 41 amu greater than the expected oligonucleotide molecule. The impurity has been found to arise by conversion of a protected guanine nucleobase to N-2-acetyl-2,6-diaminopurine. A two-part mechanism is proposed consisting of transamidation of the protecting group on guanine and substitution of guanine's O-6 atom. (C) 2014 Elsevier Ltd. All rights reserved.