5'-O--5-<3-oxo-3-<<2-<<1-oxo-2,6-bis<(trifluoroacetyl)amino>hexyl>amino>-ethyl>amino>propyl>-2'-deoxyuridine 3'-O-(N,N-diisopropylamino)(β-cyanoethoxy)phosphine | 132776-85-3

• 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: 5'-O--5-<3-oxo-3-<<2-<<1-oxo-2,6-bis<(trifluoroacetyl)amino>hexyl>amino>-ethyl>amino>propyl>-2'-deoxyuridine 3'-O-(N,N-diisopropylamino)(β-cyanoethoxy)phosphine
• 英文别名: (2S)-N-[2-[3-[1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxyoxolan-2-yl]-2,4-dioxopyrimidin-5-yl]propanoylamino]ethyl]-2,6-bis[(2,2,2-trifluoroacetyl)amino]hexanamide
• CAS: 132776-85-3；132776-98-8
• 化学式: C₅₄H₆₇F₆N₈O₁₂P
• 分子量: 1165.14
• InChiKey: ZBYSMNAHBXSMFR-MRJIUUFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.57
• 重原子数：
  81.0
• 可旋转键数：
  30.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  253.67
• 氢给体数：
  5.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  5'-O--5-<3-oxo-3-<<2-<<1-oxo-2,6-bis<(trifluoroacetyl)amino>hexyl>amino>-ethyl>amino>propyl>-2'-deoxyuridine 3'-O-(N,N-diisopropylamino)(β-cyanoethoxy)phosphine 生成 [(2R,3S,5R)-5-[5-[3-[2-[[(2S)-2,6-diaminohexanoyl]amino]ethylamino]-3-oxopropyl]-2,4-dioxopyrimidin-1-yl]-2-(hydroxymethyl)oxolan-3-yl] [(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl hydrogen phosphate
  参考文献：
  名称：

  BASHKIN, JAMES K.;MCBEATH, RANDY J.;MODAK, ANIL S.;SAMPLE, KIRBY R.;WISE,+, J. ORG. CHEM., 56,(1991) N, C. 3168-3176

  摘要：

  DOI：
• 作为产物：
  描述：

  bis(trifluoroacetyl)L-Lys-OH 在 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 28.83h， 生成 5'-O--5-<3-oxo-3-<<2-<<1-oxo-2,6-bis<(trifluoroacetyl)amino>hexyl>amino>-ethyl>amino>propyl>-2'-deoxyuridine 3'-O-(N,N-diisopropylamino)(β-cyanoethoxy)phosphine
  参考文献：
  名称：

  Synthesis and characterization of oligonucleotide peptides

  摘要：

  The transport and reactivity of oligonucleotides may be altered by attaching pendant peptides, and it is of interest to develop general synthetic methods for such bioconjugates. Two protecting group strategies are described for the synthesis of nucleotide peptides containing a lysine residue. The preparation of a lysine-nucleopeptide phosphoramidite reagent is described, along with its use in solid-phase DNA synthesis. Di- and trinucleotides were prepared with pendant and extensively characterized by NMR. These studies showed the peptide side chains to have survived DNA synthesis conditions; we then incorporated nucleopeptide residues into longer oligonucleotides. A similar approach is described for the preparation of oligonucleotide histidines. Previously reported histidine-nucleopeptides serve as precursors to phosphoramidites and to phosphodiester DNA building blocks. Both solution- and solid-phase techniques are presented for the preparation of histidine-containing oligonucleotides. The methodology developed here allows the incorporation of nucleopeptide residues at internal positions in a DNA sequence, using standard reagents. We present a complete description of the synthesis, purification, and characterization (via mass spectral and NMR methods) of the novel compounds.

  DOI：

  10.1021/jo00009a044