(3S,4R)-1-(N-tert-butoxycarbonyl)-3-(9H-fluoren-9-yl-methoxycarbonylamino)pyrrolidine-4-carboxylic acid pentafluorophenyl ester | 1345261-76-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (3S,4R)-1-(N-tert-butoxycarbonyl)-3-(9H-fluoren-9-yl-methoxycarbonylamino)pyrrolidine-4-carboxylic acid pentafluorophenyl ester
• CAS: 1345261-76-8
• 化学式: C₃₁H₂₇F₅N₂O₆
• 分子量: 618.557
• InChiKey: VAGZKQWZGVXNSH-TZIWHRDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.06
• 重原子数：
  44.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  94.17
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  在 盐酸 、 palladium on activated charcoal 、 水 、 氢气 、 sodium cyanoborohydride 、 碳酸氢钠 、 N,N-二异丙基乙胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 丙酮 为溶剂， 反应 0.5h， 生成 (3S,4R)-1-(N-tert-butoxycarbonyl)-3-(9H-fluoren-9-yl-methoxycarbonylamino)pyrrolidine-4-carboxylic acid pentafluorophenyl ester
  参考文献：
  名称：

  3-Aminopyrrolidine-4-carboxylic acid as versatile handle for internal labeling of pyrrolidinyl PNA

  摘要：

  Conformationally restricted pyrrolidinyl PNAs with an alpha/beta-dipeptide backbone consisting of a nucleobase-modified proline and a cyclic five-membered amino acid spacer such as (1S,2S)-2-aminocyclopentanecarboxylic acid (ACPC) (acpcPNA) can form very stable hybrids with DNA with high Watson-Crick base pairing specificity. This work aims to explore the effect of incorporating 3-aminopyrrolidine-4-carboxylic acid (APC), which is isosteric to the ACPC spacer, into the acpcPNA. It is expected that the modification should not negatively affect the DNA binding properties, and that the additional nitrogen atom in the APC should provide a handle for internal modification. Orthogonally-protected (N-3-Fmoc/N-1-Boc and N-3-Fmoc/N-1-Tfa) APC monomers have been successfully synthesized and incorporated into the acpcPNA by Fmoc-solid-phase peptide synthesis. T-m, UV and CD spectroscopy confirmed that the (3R,4S)-APC could substitute the (1S,2S)-ACPC spacer in the acpcPNA with only slightly decreasing the stability of the hybrids formed between the modified acpc/apcPNA and DNA. In contrast, the (3S,4R) enantiomer of APC caused substantial destabilization of the hybrids. Furthermore, a successful on-solid-support internal labeling of the acpc/apcPNA via amide bond formation between pyrene-1-carboxylic acid or 4-(pyrene-1-yl) butyric acid and the pyrrolidine nitrogen atom of the APC spacer has been demonstrated. Fluorescence properties of the pyrene-labeled acpc/apcPNAs are sensitive to their hybridization states and can readily distinguish between complementary and single-mismatched DNA targets. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.08.079