N-(tert-butoxycarbonyl)-(4'R)-p-toluenesulfonyloxy-(2'R)-proline diphenylmethyl ester | 1257225-15-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(tert-butoxycarbonyl)-(4'R)-p-toluenesulfonyloxy-(2'R)-proline diphenylmethyl ester
• CAS: 1257225-15-2
• 化学式: C₃₀H₃₃NO₇S
• 分子量: 551.661
• InChiKey: AOFNGIKTWKPHRW-AOYPEHQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.41
• 重原子数：
  39.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  99.21
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  N-(tert-butoxycarbonyl)-(4'R)-p-toluenesulfonyloxy-(2'R)-proline diphenylmethyl ester 、 腺嘌呤 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以72%的产率得到N-(tert-butoxycarbonyl)-(4'S)-adenin-9-yl-(2'R)-proline diphenylmethyl ester
  参考文献：
  名称：

  DNA-, RNA- and self-pairing properties of a pyrrolidinyl peptide nucleic acid with a (2′R,4′S)-prolyl-(1S,2S)-2-aminocyclopentanecarboxylic acid backbone

  摘要：

  A new pyrrolidinyl peptide nucleic acid (PNA) comprising of an alternate sequence of 4'-nucleobase-modified proline with (2'R,4'S) configuration and a (1S,2S)-2-aminocyclopentanecarboxylic acid [(2'R,4'S)-acpcPNA] backbone was synthesized and its DNA-, RNA- and self-pairing properties studied. T-m and CD studies suggested that the (2'R,4'S)-acpcPNA forms antiparallel hybrids to DNA and RNA with high sequence and direction specificity. The stability of these hybrids is comparable to those of the (2'R,4'R)-acpcPNA hybrids previously reported by our group. On the other hand, experiments with a self-complementary sequence indicated that the new (2'R,4'S)-acpcPNA forms a more stable antiparallel self-hybrid than (2'R,4'R)-acpcPNA. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.08.102
• 作为产物：
  描述：

  对甲苯磺酰氯 、 1-(1,1-dimethylethyl) 2-(diphenylmethyl) (2R,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate 在 4-二甲氨基吡啶 、 三乙胺 作用下， 反应 6.0h， 以83%的产率得到N-(tert-butoxycarbonyl)-(4'R)-p-toluenesulfonyloxy-(2'R)-proline diphenylmethyl ester
  参考文献：
  名称：

  DNA-, RNA- and self-pairing properties of a pyrrolidinyl peptide nucleic acid with a (2′R,4′S)-prolyl-(1S,2S)-2-aminocyclopentanecarboxylic acid backbone

  摘要：

  A new pyrrolidinyl peptide nucleic acid (PNA) comprising of an alternate sequence of 4'-nucleobase-modified proline with (2'R,4'S) configuration and a (1S,2S)-2-aminocyclopentanecarboxylic acid [(2'R,4'S)-acpcPNA] backbone was synthesized and its DNA-, RNA- and self-pairing properties studied. T-m and CD studies suggested that the (2'R,4'S)-acpcPNA forms antiparallel hybrids to DNA and RNA with high sequence and direction specificity. The stability of these hybrids is comparable to those of the (2'R,4'R)-acpcPNA hybrids previously reported by our group. On the other hand, experiments with a self-complementary sequence indicated that the new (2'R,4'S)-acpcPNA forms a more stable antiparallel self-hybrid than (2'R,4'R)-acpcPNA. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.08.102

文献信息

• DNA-, RNA- and self-pairing properties of a pyrrolidinyl peptide nucleic acid with a (2′R,4′S)-prolyl-(1S,2S)-2-aminocyclopentanecarboxylic acid backbone
  作者：Jaru Taechalertpaisarn、Pitchanun Sriwarom、Chalotorn Boonlua、Nattawut Yotapan、Chotima Vilaivan、Tirayut Vilaivan

  DOI：10.1016/j.tetlet.2010.08.102

  日期：2010.11

  A new pyrrolidinyl peptide nucleic acid (PNA) comprising of an alternate sequence of 4'-nucleobase-modified proline with (2'R,4'S) configuration and a (1S,2S)-2-aminocyclopentanecarboxylic acid [(2'R,4'S)-acpcPNA] backbone was synthesized and its DNA-, RNA- and self-pairing properties studied. T-m and CD studies suggested that the (2'R,4'S)-acpcPNA forms antiparallel hybrids to DNA and RNA with high sequence and direction specificity. The stability of these hybrids is comparable to those of the (2'R,4'R)-acpcPNA hybrids previously reported by our group. On the other hand, experiments with a self-complementary sequence indicated that the new (2'R,4'S)-acpcPNA forms a more stable antiparallel self-hybrid than (2'R,4'R)-acpcPNA. (C) 2010 Elsevier Ltd. All rights reserved.