1-(N-Boc-aminoethyl)-5-(R)-(thymin-1-yl)-2-(S)-pipecolic acid | 695183-62-1

• 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-Boc-aminoethyl)-5-(R)-(thymin-1-yl)-2-(S)-pipecolic acid
• 英文别名: (2S,5R)-1-[2-(N-tert-butoxycarbonylamino)ethyl]-5-(thymin-1-yl)pipecolic acid；(2S,5R)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-1-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]piperidine-2-carboxylic acid
• CAS: 695183-62-1
• 化学式: C₁₈H₂₈N₄O₆
• 分子量: 396.444
• InChiKey: JWSSBWLMAFTNBY-OLZOCXBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  128
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Boc-beta-丙氨酸 、 N-[2-(3,4-二氢-5-甲基-2,4-二氧代-1(2H)-嘧啶基)乙酰基]-N-[2-[[(1,1-二甲基乙氧基)羰基]氨基]乙基]-甘氨酸 、 1-(N-Boc-aminoethyl)-5-(R)-(thymin-1-yl)-2-(S)-pipecolic acid 生成 3-[[2-[2-[[2-[2-[[2-[2-[[2-[2-[[2-[2-[[2-[2-[[2-[2-[[[(2S,5R)-1-(2-aminoethyl)-5-(4-hydroxy-5-methyl-2-oxopyrimidin-1-yl)piperidin-2-yl]-hydroxymethylidene]amino]ethyl-[2-(4-hydroxy-5-methyl-2-oxopyrimidin-1-yl)acetyl]amino]-1-hydroxyethylidene]amino]ethyl-[2-(4-hydroxy-5-methyl-2-oxopyrimidin-1-yl)acetyl]amino]-1-hydroxyethylidene]amino]ethyl-[2-(4-hydroxy-5-methyl-2-oxopyrimidin-1-yl)acetyl]amino]-1-hydroxyethylidene]amino]ethyl-[2-(4-hydroxy-5-methyl-2-oxopyrimidin-1-yl)acetyl]amino]-1-hydroxyethylidene]amino]ethyl-[2-(4-hydroxy-5-methyl-2-oxopyrimidin-1-yl)acetyl]amino]-1-hydroxyethylidene]amino]ethyl-[2-(4-hydroxy-5-methyl-2-oxopyrimidin-1-yl)acetyl]amino]-1-hydroxyethylidene]amino]ethyl-[2-(4-hydroxy-5-methyl-2-oxopyrimidin-1-yl)acetyl]amino]-1-hydroxyethylidene]amino]propanoic acid
  参考文献：
  名称：

  (2S,5R/2R,5S)-Aminoethylpipecolyl aepip-aegPNA chimera: synthesis and duplex/triplex stability

  摘要：

  This article reports the design and facile synthesis of novel chiral six-membered PNA analogues (2S,5R/2R,5S)-1-(N-Boc-aminoethyl)-5-(thymin-1-yl)pipecolic acid, aepipPNA IV that upon incorporation into standard aegPNA sequences effected stabilization of complexes with complementary target DNA. Substitution of aegPNA unit by the designed monomer at the C-terminus was more effective than substitution at N-terminus. The stabilizing behaviour improved with degree of substitution and was found to be dependent on their relative positions in the sequence. The six-membered piperidine ring in the design may freeze the rigid chair conformations and the relative stereochemistry of the substituents may in effect direct the complex formation with DNA/RNA by sequence-specific nucleobase recognition. In the present aepipPNA analogues, the L-trans stereochemical disposition of the substituents seems to lead to the favorable pre-organization of the PNA oligomers for complex formation with DNA. The results reported here further expand the repertoire of cyclic PNA analogues. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2004.07.080
• 作为产物：
  描述：

  (2S,5S)-5-羟基-2-哌啶羧酸甲酯 在 sodium hydroxide 、 偶氮二甲酸二异丙酯 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 24.0h， 生成 1-(N-Boc-aminoethyl)-5-(R)-(thymin-1-yl)-2-(S)-pipecolic acid
  参考文献：
  名称：

  并入（2 S，5 R）-氨乙基胡椒基单元的嵌合肽核酸：合成和DNA结合研究

  摘要：

  新型手性六元PNA类似物（2 S，5 R）-1-（N -Boc-氨基乙基）-5-（胸腺嘧啶-1-基）哌酸aepip PNA的设计和合成进入PNA序列可实现与靶互补DNA复合物的稳定化。这是第一个例子，其中六元PNA能够与DNA形成稳定的复合物，并进一步扩展了环状PNA类似物的组成。

  DOI：

  10.1016/j.tetlet.2004.02.099

文献信息

• Chimeric peptide nucleic acids incorporating (2S,5R)-aminoethyl pipecolyl units: synthesis and DNA binding studies
  作者：Pravin S. Shirude、Vaijayanti A. Kumar、Krishna N. Ganesh

  DOI：10.1016/j.tetlet.2004.02.099

  日期：2004.4

  The design and facile synthesis of a novel chiral six-membered PNA analogue (2S,5R )-1-(N-Boc-aminoethyl)-5-(thymin-1-yl)pipecolic acid, aepipPNA, that upon incorporation into PNA sequences effected stabilization of complexes with target complementary DNA. This is the first example where a six membered-PNA is shown to be capable of forming stable complexes with DNA and further expands the repertoire

  新型手性六元PNA类似物（2 S，5 R）-1-（N -Boc-氨基乙基）-5-（胸腺嘧啶-1-基）哌酸aepip PNA的设计和合成进入PNA序列可实现与靶互补DNA复合物的稳定化。这是第一个例子，其中六元PNA能够与DNA形成稳定的复合物，并进一步扩展了环状PNA类似物的组成。
• (2S,5R/2R,5S)-Aminoethylpipecolyl aepip-aegPNA chimera: synthesis and duplex/triplex stability
  作者：Pravin S. Shirude、Vaijayanti A. Kumar、Krishna N. Ganesh

  DOI：10.1016/j.tet.2004.07.080

  日期：2004.10

  This article reports the design and facile synthesis of novel chiral six-membered PNA analogues (2S,5R/2R,5S)-1-(N-Boc-aminoethyl)-5-(thymin-1-yl)pipecolic acid, aepipPNA IV that upon incorporation into standard aegPNA sequences effected stabilization of complexes with complementary target DNA. Substitution of aegPNA unit by the designed monomer at the C-terminus was more effective than substitution at N-terminus. The stabilizing behaviour improved with degree of substitution and was found to be dependent on their relative positions in the sequence. The six-membered piperidine ring in the design may freeze the rigid chair conformations and the relative stereochemistry of the substituents may in effect direct the complex formation with DNA/RNA by sequence-specific nucleobase recognition. In the present aepipPNA analogues, the L-trans stereochemical disposition of the substituents seems to lead to the favorable pre-organization of the PNA oligomers for complex formation with DNA. The results reported here further expand the repertoire of cyclic PNA analogues. (C) 2004 Published by Elsevier Ltd.