2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-N⁴-isobutyrylcytidine 3'-[N,N-diisopropyl-P-(4-phenylbutyl)phosphonamidite]

• 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: 2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-N⁴-isobutyrylcytidine 3'-[N,N-diisopropyl-P-(4-phenylbutyl)phosphonamidite]
• 英文别名: N-[1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[[di(propan-2-yl)amino]-(4-phenylbutyl)phosphanyl]oxyoxolan-2-yl]-2-oxopyrimidin-4-yl]-2-methylpropanamide
• 化学式: C₅₀H₆₃N₄O₇P
• 分子量: 863.047
• InChiKey: BITSFOPEILHQII-JFGNCXTPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  62
• 可旋转键数：
  21
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  4-苯基-1-丁基溴 在 magnesium 、 N,N-二异丙基乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 10.5h， 生成 2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-N⁴-isobutyrylcytidine 3'-[N,N-diisopropyl-P-(4-phenylbutyl)phosphonamidite]
  参考文献：
  名称：

  Synthesis and Properties of Nonpolar DNA (Arylalkyl)phosphonates

  摘要：

  The eight (arylalkyl)-modified phosphoramidites (=(arylalkyl)phosphonamidites) 1-8 (Fig. 2) were synthesized (Schemes 1-3) and incorporated at different positions into 2'-deoxyoligonucleotides. The [P(R)]and [P(S)]-diastereoisomers of the hexanucleotides 32-39 (Table 1) and of the dodecanucleotides 41-45 (Table 2) obtained were separated by means of reversed-phase HPLC. UV, CD, and fluorescence spectroscopy were used to investigate the thermal stability (T-m) and the structural changes of their DNA duplexes with 5'-d(CGCGCG)-3' and 5'-d(ATGATTGACCTG)-3', respectively. The T-m values significantly depend on the place of modification (Table 2). A dangling-end effect is observed when the [3-(anthracen-9-yl)propyl]-modified 8 is attached at the 5'-terminus (see duplex with 45c). In the case of the incorporation of aromatic moieties tethered via a methylene linker to the P-atom (benzyl- and (naphthalen-1-ylmethyl)-modified 1 and 6, resp.), the duplexes with the [P(R)]-oligonucleotides are more stable than those with the [P(S)]-isomers, whereas in the case of longer alkyl chains at the P-atom (see 2-5), the T-m values show the reverse tendency. The observed T-m differences are assigned to changes in base stacking (Figs. 6 and 7).

  DOI：

  10.1002/1522-2675(200208)85:8<2503::aid-hlca2503>3.0.co;2-i

文献信息

• Synthesis and Properties of Nonpolar DNA (Arylalkyl)phosphonates
  作者：Stefan Amberg、Joachim W. Engels

  DOI：10.1002/1522-2675(200208)85:8<2503::aid-hlca2503>3.0.co;2-i

  日期：2002.8

  The eight (arylalkyl)-modified phosphoramidites (=(arylalkyl)phosphonamidites) 1-8 (Fig. 2) were synthesized (Schemes 1-3) and incorporated at different positions into 2'-deoxyoligonucleotides. The [P(R)]and [P(S)]-diastereoisomers of the hexanucleotides 32-39 (Table 1) and of the dodecanucleotides 41-45 (Table 2) obtained were separated by means of reversed-phase HPLC. UV, CD, and fluorescence spectroscopy were used to investigate the thermal stability (T-m) and the structural changes of their DNA duplexes with 5'-d(CGCGCG)-3' and 5'-d(ATGATTGACCTG)-3', respectively. The T-m values significantly depend on the place of modification (Table 2). A dangling-end effect is observed when the [3-(anthracen-9-yl)propyl]-modified 8 is attached at the 5'-terminus (see duplex with 45c). In the case of the incorporation of aromatic moieties tethered via a methylene linker to the P-atom (benzyl- and (naphthalen-1-ylmethyl)-modified 1 and 6, resp.), the duplexes with the [P(R)]-oligonucleotides are more stable than those with the [P(S)]-isomers, whereas in the case of longer alkyl chains at the P-atom (see 2-5), the T-m values show the reverse tendency. The observed T-m differences are assigned to changes in base stacking (Figs. 6 and 7).