5-oxo-N-benzyloxycarbonyl-2-(R)-pipecolic acid methyl ester

• 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: 5-oxo-N-benzyloxycarbonyl-2-(R)-pipecolic acid methyl ester
• 英文别名: (R)-1-Benzyl2-methyl5-oxopiperidine-1,2-dicarboxylate；1-O-benzyl 2-O-methyl (2R)-5-oxopiperidine-1,2-dicarboxylate
• 化学式: C₁₅H₁₇NO₅
• 分子量: 291.304
• InChiKey: HFKHJRQXLOFHNO-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-oxo-N-benzyloxycarbonyl-2-(R)-pipecolic acid methyl ester 在 palladium on activated charcoal sodium tetrahydroborate 、 氢气 作用下， 以 甲醇 为溶剂， 生成 methyl (2R,5R)-5-hydroxypiperidine-2-carboxylate
  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：

  N-[苄氧羰基]-D-谷氨酸 1-甲基酯 在 dirhodium tetraacetate 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 苯 为溶剂， 生成 5-oxo-N-benzyloxycarbonyl-2-(R)-pipecolic acid methyl ester
  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

文献信息

• (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.