(R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-(2-nitro-benzenesulfonylamino)-propionic acid | 487027-90-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-(2-nitro-benzenesulfonylamino)-propionic acid
• 英文别名: Fmoc-D-Dap(Ns)-OH；(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[(2-nitrophenyl)sulfonylamino]propanoic acid
• CAS: 487027-90-7
• 化学式: C₂₄H₂₁N₃O₈S
• 分子量: 511.512
• InChiKey: PAMPDZSGJFJAFO-HXUWFJFHSA-N

物化性质

• 密度：
  1.463±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  176
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-(2-nitro-benzenesulfonylamino)-propionic acid 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成
  参考文献：
  名称：

  Synthetic strategy for side chain mono-N-alkylation of Fmoc-amino acids promoted by molecular sieves

  摘要：

  A new synthetic strategy to alkylate amino groups under mild conditions has been developed. It utilizes only 4 angstrom molecular sieves as base in order to promote the N-alkylation reaction, in presence of the appropriate alkyl halide. The methodology was validated by the simple and efficient side-chain N-alkylation of o-Ns-protected Fmoc-amino acid. One of them was introduced as building block into a peptide sequence, thus allowing the preparation of site-specific alkylated peptide molecules.

  DOI：

  10.1007/s00726-010-0798-6
• 作为产物：
  描述：

  Fmoc-D-天冬酰胺 在 吡啶 、 甲醇 、 三乙胺 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.0h， 生成 (R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-(2-nitro-benzenesulfonylamino)-propionic acid
  参考文献：
  名称：

  Solid-Phase Synthesis of Amine-Bridged Cyclic Enkephalin Analogues via On-Resin Cyclization Utilizing the Fukuyama−Mitsunobu Reaction

  摘要：

  An efficient solid-phase synthetic route is described for the preparation of 13-membered amine-bridged cyclic enkephalin analogues (ABEs) 1a and 1c-1j (Figure 1) resulting from a sulfonamide-containing peptide whose backbone is bound to a resin. The Fukuyama-Mitsunobu reaction of the 2-nitrobenzenesulfonyl-protected amine bound to the solid support with protected aminoethanol in the presence of triphenylphosphine and diisopropyl azodicarboxylate (DIAD) is utilized to prepare a resin-bound sulfonamide-protected secondary amine. After peptide cyclization, this protected amine functionality becomes the "amine bridge" of the target molecule. In addition, the reagent DIAD was found to be a superior reagent compared to diethyl azodicarboxylate (DEAD) in the solid-phase Fukuyama-Mitsunobu reaction.

  DOI：

  10.1021/jo020447l

文献信息

• Solid-Phase Synthesis of Amine-Bridged Cyclic Enkephalin Analogues via On-Resin Cyclization Utilizing the Fukuyama−Mitsunobu Reaction
  作者：Yosup Rew、Murray Goodman

  DOI：10.1021/jo020447l

  日期：2002.12.1

  An efficient solid-phase synthetic route is described for the preparation of 13-membered amine-bridged cyclic enkephalin analogues (ABEs) 1a and 1c-1j (Figure 1) resulting from a sulfonamide-containing peptide whose backbone is bound to a resin. The Fukuyama-Mitsunobu reaction of the 2-nitrobenzenesulfonyl-protected amine bound to the solid support with protected aminoethanol in the presence of triphenylphosphine and diisopropyl azodicarboxylate (DIAD) is utilized to prepare a resin-bound sulfonamide-protected secondary amine. After peptide cyclization, this protected amine functionality becomes the "amine bridge" of the target molecule. In addition, the reagent DIAD was found to be a superior reagent compared to diethyl azodicarboxylate (DEAD) in the solid-phase Fukuyama-Mitsunobu reaction.
• Synthetic strategy for side chain mono-N-alkylation of Fmoc-amino acids promoted by molecular sieves
  作者：Luca Monfregola、Stefania De Luca

  DOI：10.1007/s00726-010-0798-6

  日期：2011.10

  A new synthetic strategy to alkylate amino groups under mild conditions has been developed. It utilizes only 4 angstrom molecular sieves as base in order to promote the N-alkylation reaction, in presence of the appropriate alkyl halide. The methodology was validated by the simple and efficient side-chain N-alkylation of o-Ns-protected Fmoc-amino acid. One of them was introduced as building block into a peptide sequence, thus allowing the preparation of site-specific alkylated peptide molecules.