1-(N-[2-(tert-butoxycarbonylamino)ethyl])-4-(R)-hydroxy-2-(S)-proline methyl ester | 253307-68-5

• 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-[2-(tert-butoxycarbonylamino)ethyl])-4-(R)-hydroxy-2-(S)-proline methyl ester
• 英文别名: N-Boc-aminoethyl-4-(R)-hydroxy-2-(S)-proline methyl ester；1-N-(2-(Boc-amino)ethyl)-4R-hydroxy-2S-proline methyl ester；(2S,4R)-Methyl 1-(2-((tert-butoxycarbonyl)amino)ethyl)-4-hydroxypyrrolidine-2-carboxylate；methyl (2S,4R)-4-hydroxy-1-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]pyrrolidine-2-carboxylate
• CAS: 253307-68-5
• 化学式: C₁₃H₂₄N₂O₅
• 分子量: 288.344
• InChiKey: UOGCRAACOYHBDM-ZJUUUORDSA-N

物化性质

• 沸点：
  426.1±45.0 °C(Predicted)
• 密度：
  1.168±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  88.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(N-[2-(tert-butoxycarbonylamino)ethyl])-4-(R)-hydroxy-2-(S)-proline methyl ester 在 ruthenium trichloride sodium periodate 、 18-冠醚-6 、 potassium carbonate 、 三乙胺 作用下， 以 四氯化碳 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 0.33h， 生成 (2S,4S)-4-(6-Benzoyloxycarbonylamino-purin-9-yl)-1-(2-tert-butoxycarbonylamino-ethyl)-5-oxo-pyrrolidine-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Expanding the repertoire of pyrrolidyl PNA analogues for DNA/RNA hybridization selectivity: aminoethylpyrrolidinone PNA (aepone-PNA)

  摘要：

  新的PNA类似物源自氨基乙基吡咯烷-5-酮骨架，相较于未修饰的PNA，显示出对aepone-PNA:DNA杂交物的稳定性和对相应RNA杂交物的去稳定性。

  DOI：

  10.1039/b307362a
• 作为产物：
  描述：

  L-羟基脯氨酸 在 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 生成 1-(N-[2-(tert-butoxycarbonylamino)ethyl])-4-(R)-hydroxy-2-(S)-proline methyl ester
  参考文献：
  名称：

  杂合DNA i-基序：氨乙基脯氨酰-PNA（pC 5）增强了DNA（dC 5）i-基序结构的稳定性

  摘要：

  本报告描述C-丰富序列的合成，五聚体胞嘧啶，的AEP -PNA及其对形成杂化DNA的生物物理研究：AEP -PNAi基序结构与DNA胞嘧啶五聚体（DC 5酸性pH条件下）。这里，CD / UV / NMR / ESI-质谱研究强烈支持稳定的杂交DNA的i-基序结构的与地层AEP -PNA即使接近酸性条件。因此AEP -PNA C-丰富序列胞嘧啶可以被认为是潜在的DNA的i-基序的稳定剂在体内的条件。

  DOI：

  10.1016/j.bmcl.2017.11.004

文献信息

• Aminoethylprolyl Peptide Nucleic Acids (aepPNA):  Chiral PNA Analogues That Form Highly Stable DNA:aepPNA₂ Triplexes
  作者：Moneesha D'Costa、Vaijayanti A. Kumar、Krishna N. Ganesh

  DOI：10.1021/ol990835i

  日期：1999.11.1

  [GRAPHICS]The replacement of the glycyl component in the peptide nucleic acid (PNA) backbone by a prolyl unit bearing a nucleobase leads to the aminoethylprolyl (aep) PNAs, which are chiral and cationic. The homooligomeric aepPNA binds to complementary DNA sequences with high affinity and sequence specificity, forming highly stable triplexes.
• Regioselective oxidation of N -alkylpyrrolidines to pyrrolidin-5-ones by RuCl 3 /NaIO 4
  作者：Nagendra K. Sharma、Krishna N. Ganesh

  DOI：10.1016/j.tetlet.2003.12.072

  日期：2004.2

  RuCl3/NaIO4 under EtOAc/H2O biphasic conditions, selectively oxidizes the Nalpha-endo-methylene group of pyrrolidine derivatives, without affecting the exo-methylene group adjacent to the N-heteroatom. (C) 2003 Elsevier Ltd. All rights reserved.
• N7-Guanine as a C⁺ Mimic in Hairpin <i>a</i><i>eg</i>/<i>a</i><i>ep</i>PNA-DNA Triplex:  Probing Binding Selectivity by UV-T<i>_m</i> and Kinetics by Fluorescence-Based Strand-Invasion Assay
  作者：Moneesha D'Costa、Vaijayanti A. Kumar、Krishna N. Ganesh

  DOI：10.1021/jo034048h

  日期：2003.5.1

  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.
• Aminoethylprolyl (<i>a</i><i>ep</i>) PNA:  Mixed Purine/Pyrimidine Oligomers and Binding Orientation Preferences for PNA:DNA Duplex Formation
  作者：Moneesha D'Costa、Vaijayanti Kumar、Krishna N. Ganesh

  DOI：10.1021/ol015546k

  日期：2001.5.1

  [GRAPHICS]The synthesis of (2S,4S)- and (PR,4S)-aepPNA monomers of adenine, guanine, and cytosine (3-5) end their incorporation at appropriate positions into aegPNA sequence 7 leads to mixed aeg-aep backbone/mixed nucleobase PNAs 8-11, The thermal stabilities of the derived duplexes with DNA are found to be dependent on nucleobase and backbone stereochemistry.
• ENGINEERING PREFERENCES OF HAIRPIN PNA BINDING TO COMPLEMENTARY DNA: EFFECT OF N7G IN<i>aeg</i>/<i>aep</i>PNA BACKBONE
  作者：V. A. Kumar、M. D'Costa、K. N. Ganesh

  DOI：10.1081/ncn-100002516

  日期：2001.3.31

  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.