Fmoc-L-2',6'-dimethylphenylalanine | 911813-85-9

• 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: Fmoc-L-2',6'-dimethylphenylalanine
• 英文别名: (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(2,6-dimethylphenyl)propanoic acid；Fmoc-2,6-Dimethyl-L-Phenylalanine；(2S)-3-(2,6-dimethylphenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
• CAS: 911813-85-9
• 化学式: C₂₆H₂₅NO₄
• 分子量: 415.489
• InChiKey: SONZSWVVQNNLAB-DEOSSOPVSA-N

物化性质

• 沸点：
  641.1±55.0 °C(Predicted)
• 密度：
  1.236±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-芴甲氧羰基-2,6-二甲基-L-酪氨酸 、 Fmoc-L-2',6'-dimethylphenylalanine 、 Fmoc-Lys(Boc)-NH2 、 N’-[(2,3-二氢-2,2,4,6,7-五甲基苯并呋喃-5-基)磺酰基]-N-芴甲氧羰基-D-精氨酸 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 、 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.08h， 以73.1 mg的产率得到H-Tyr(2,6-diMe)-D-Arg-Phe(2,6-diMe)-Lys-NH2
  参考文献：
  名称：

  [Dmt1]DALDA analogues with enhanced μ opioid agonist potency and with a mixed μ/κ opioid activity profile

  摘要：

  Analogues of [Dmt(1)]DALDA (H-Dmt-D-Arg-Phe-Lys-NH2; Dmt = 2',6'-dimethyltyrosine), a potent mu opioid agonist peptide with mitochondria-targeted antioxidant activity, were prepared by replacing Phe(3) with various 2',6'-dialkylated Phe analogues, including 2',6'-dimethylphenylalanine (Dmp), 2',4',6'-trimethylphenylalanine (Tmp), 2'-isopropyl-6'-methylphenylalanine (Imp) and 2'-ethyl-6'-methylphenylalanine (Emp), or with the bulky amino acids 3'-(1-naphthyl)alanine (1-Nal), 3'-(2-naphthyl)alanine (2-Nal) or Trp. Several compounds showed significantly increased mu agonist potency, retained mu receptor selectivity and are of interest as drug candidates for neuropathic pain treatment. Surprisingly, the Dmp(3)-, Imp(3)-, Emp(3)- and 1-Nal(3)-containing analogues showed much increased kappa receptor binding affinity and had mixed mu/kappa properties. In these cases, molecular dynamics studies indicated conformational preorganization of the unbound peptide ligands due to rotational restriction around the C-beta-C-gamma bond of the Xxx(3) residue, in correlation with the observed kappa receptor binding enhancement. Compounds with a mixed mu/kappa opioid activity profile are known to have therapeutic potential for treatment of cocaine abuse. (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.02.011
• 作为产物：
  描述：

  1,3-二甲基-2-碘苯 在 palladium on activated charcoal 盐酸 、 palladium diacetate 、 sodium hydroxide 、 氢气 、 sodium carbonate 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 三(邻甲基苯基)磷 作用下， 以 1,4-二氧六环 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 70.0 ℃ 、405.3 kPa 条件下， 反应 45.0h， 生成 Fmoc-L-2',6'-dimethylphenylalanine
  参考文献：
  名称：

  Enkephalin analogues with 2′,6′-dimethylphenylalanine replacing phenylalanine in position 4

  摘要：

  Four Leu-enkephalin (Enk) analogues containing 2'.6'-dimethyphenylalanine (Dmp) in position 4 were prepared and tested for their receptor binding and biological activities. Among the analogues prepared, [2', 6'-dimethvltyrosine(1), D-Dmp(4)]Enk was found to be an antagonist toward mu and delta opioid receptors with pA(2) values of 6.90 and 5.57, respectively. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00665-x

文献信息

• Synthesis of 2,6-Dimethyltyrosine-Like Amino Acids through Pinacolinamide-Enabled C–H Dimethylation of 4-Dibenzylamino Phenylalanine
  作者：Davide Illuminati、Anna Fantinati、Tiziano De Ventura、Daniela Perrone、Chiara Sturaro、Valentina Albanese、Erika Marzola、Virginia Cristofori、Julie Oble、Giovanni Poli、Claudio Trapella

  DOI：10.1021/acs.joc.1c02527

  日期：2022.3.4

  carrying methyl groups at positions 2 and 6 and diverse functionalities at position 4 has been achieved. The approach, which took advantage of a Pd-catalyzed directed C–H dimethylation of picolinamide derivatives, allowed the electronic and steric properties of the resulting amino acid derivatives to be altered by appending a variety of electron-withdrawing, electron-donating, or bulky groups.

  已经实现了在 2 位和 6 位带有甲基基团和在 4 位具有多种官能团的NH -Boc-或NH -Fmoc-保护的 L-苯丙氨酸的小型文库的合成。该方法利用 Pd 催化的甲基吡啶酰胺衍生物的定向 C-H 二甲基化，通过添加各种吸电子、给电子或庞大的物质，可以改变所得氨基酸衍生物的电子和空间特性。团体。