1-(N-[tert-butoxycarbonylaminoethyl])-4-(S)-(N²-isobutyrylguanin-7-yl)-(2S)-proline methyl ester | 340961-35-5

• 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: 1-(N-[tert-butoxycarbonylaminoethyl])-4-(S)-(N²-isobutyrylguanin-7-yl)-(2S)-proline methyl ester
• 英文别名: 1-(N-Boc-aminoethyl)-4(S)-(N²-isobutyrylguanin-7-yl)-2(S)-proline methyl ester；methyl (2S,4S)-4-[2-(2-methylpropanoylamino)-6-oxo-1H-purin-7-yl]-1-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]pyrrolidine-2-carboxylate
• CAS: 340961-35-5
• 化学式: C₂₂H₃₃N₇O₆
• 分子量: 491.547
• InChiKey: WXIVYQRXVLGDFI-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  156
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-(N-[tert-butoxycarbonylaminoethyl])-4-(S)-(N²-isobutyrylguanin-7-yl)-(2S)-proline methyl ester 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 生成 1-(N-[2-(tert-butoxycarbonylamino)ethyl])-(4S)-(N²-isobutyrylguanin-7-yl)pyrrolidine-(2S)-carboxylic acid
  参考文献：
  名称：

  ENGINEERING PREFERENCES OF HAIRPIN PNA BINDING TO COMPLEMENTARY DNA: EFFECT OF N7G INaeg/aepPNA BACKBONE

  摘要：

  AegPNA and aepPNA monomeric units bearing the N7-guanine nucleobase as a substitute for C+ have been demonstrated to bind to a GC base-pair of a duplex in a pH-independent manner when placed in the third strand. The aepPNA backbone exerts a preference for binding in the antiparallel Hoogsteen mode over the parallel Hoogsteen mode.

  DOI：

  10.1081/ncn-100002516
• 作为产物：
  描述：

  1-(N-[2-(tert-butoxycarbonylamino)ethyl])-4-(R)-hydroxy-2-(S)-proline methyl ester 在 吡啶 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 1-(N-[tert-butoxycarbonylaminoethyl])-4-(S)-(N²-isobutyrylguanin-7-yl)-(2S)-proline methyl ester
  参考文献：
  名称：

  N7-Guanine as a C⁺ Mimic in Hairpin aeg/aepPNA-DNA Triplex:  Probing Binding Selectivity by UV-T_m and Kinetics by Fluorescence-Based Strand-Invasion Assay

  摘要：

  N7-substituted guanine (N7G) has been introduced into aminoethylglycyl bisPNA (7) as a C+ mimic to achieve pH-independent triplex formation with complementary DNA sequences. The introduction of chiral, cationic aminoethylprolyl units with C+ and C+ mimic N7G in the backbone of bisPNAs (8, 9) influenced the recognition of complementary DNA in an orientation-selective manner. A simple fluorescence assay is developed to examine the process of strand invasion of target DNA duplex by these modified bisPNAs and comparative results of the study employing triplex forming polypyrimidine (C/T) (6, 8) and purine-pyrimidine (N7G/T) mixmer-bisPNAs (7, 9) are presented.

  DOI：

  10.1021/jo034048h