Fmoc-二甲基甘氨酸 | 218926-46-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: Fmoc-二甲基甘氨酸
• 中文别名: 2-[[芴甲氧羰基]氨基]-2-乙基丁酸；芴甲氧羰基-2-氨基-2-乙基丁酸；芴甲氧羰基-2-二乙基甘氨酸；Fmoc-二甲基甘氨酸
• 英文名称: Fmoc-diethylglycine
• 英文别名: N-(9-fluorenylmethyloxycarbonyl)-α,α-diethylglycine；Fmoc-Deg-OH；2-ethyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid；2-ethyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)butanoic acid
• CAS: 218926-46-6
• 化学式: C₂₁H₂₃NO₄
• 分子量: 353.418
• InChiKey: NUABWLRFIOIRJG-UHFFFAOYSA-N

物化性质

• 熔点：
  103-105 °C
• 沸点：
  559.8±33.0 °C(Predicted)
• 密度：
  1.210±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 储存条件：
  存储条件：2-8°C，干燥。

反应信息

• 作为反应物：
  描述：

  2-(4-甲氧苯基)乙胺 、 Fmoc-二甲基甘氨酸 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 二异丙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.25h， 以70%的产率得到(9H-fluoren-9-yl)methyl 3-((4-methoxyphenethyl)carbamoyl)pentan-3-ylcarbamate
  参考文献：
  名称：

  [EN] 4-IMIDAZOLIDINONES AS KV1.5 POTASSIUM CHANNEL INHIBITORS
  [FR] 4-IMIDAZOLIDINONES UTILISÉS COMME INHIBITEURS DES CANAUX POTASSIQUES KV1.5

  摘要：

  本教导涉及到公式(I)中的4-咪唑啉酮。这些化合物可作为Kv1.5钾通道抑制剂，提供房性选择性抗心律失常活性。本教导还涉及治疗房性选择性抗心律失常的组合物和方法。

  公开号：

  WO2009079624A1
• 作为产物：
  描述：

  2-氨基-2-乙基丁酸 、 氯甲酸-9-芴基甲酯 在 sodium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 8.0h， 以40%的产率得到Fmoc-二甲基甘氨酸
  参考文献：
  名称：

  Synthesis and biological activity of nociceptin/orphanin FQ analogues substituted in position 7 or 11 with Cα,α-dialkylated amino acids

  摘要：

  Previous structure-activity and NMR studies on nociceptin/orphanin FQ (N/OFQ) demonstrated that Aib substitution of Ala(7) and/or Ala(11) increases the peptide potency through an alpha helix structure induction mechanism. On these bases we synthesised and evaluated pharmacologically in the mouse vas deferens assay a series of N/OFQ-NH2 analogues substituted in position 7 and 11 with C alpha,alpha-disubstituted cyclic, linear and branched amino acids. None of the 20 novel N/OFQ analogues produced better results than [Aib(7)]N/OFQ-NH2. Thus, this substitution was combined with other chemical modifications known to modulate peptide potency and/or efficacy generating compound 21 [Nphe(1)Aib(7) Arg(14) Lys(15)] N/OFQ-NH2 (coded as UFP- 111), compound 22 [(pF)Phe(4) Aib(7) Arg(14) Lys(15)] N/OFQ-NH2 (UFP-112) and compound 23 [Phe psi(CH2-NH)Gly(2) (pF)Phe(4)Aib(7)Arg(14)Lys(15)]N/OFQ-NH2 (UFP- 113). These novel peptides behaved as highly potent NOP receptor ligands showing full (UFP- 112) and partial (UFP- 113) agonist and pure antagonist (UFP- 111) activities in a series of in vitro functional assays performed on pharmacological preparations expressing native as well as recombinant NOP receptors. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.04.026

文献信息

• Babu, Vommina V. Suresh; Ananda, Kuppanna, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2001, vol. 40, # 1, p. 70 - 74
  作者：Babu, Vommina V. Suresh、Ananda, Kuppanna

  DOI：——

  日期：——
• Use of Onium Salt-Based Coupling Reagents in Peptide Synthesis¹
  作者：Fernando Albericio、Josep M. Bofill、Ayman El-Faham、Steven A. Kates

  DOI：10.1021/jo980807y

  日期：1998.12.1

  Peptide coupling methods derived from onium salts based on 1-hydroxybenzotriazole (HOBt) and 1-hydroxy-7-azabenzotriazole (HOAt) are becoming incorporated in synthetic strategies more frequently than the classical carbodiimide methods. We have correlated the reactivity of various onium salts derived from HOXt (X = A, B), with the structure of the reagents in question. Thus, we confirmed that the aza derivatives are more reactive than the parent benzotriazole derivatives in both activation and coupling. In addition, the activation step is determined by the structure of the carbon skeleton. Thus, pyrrolidino derivatives appear to be reagents of choice relative to the piperidino analogues or those derived from trialkylamines. Furthermore although phosphonium salts are slightly less reactive than the corresponding aminium/uronium salts, the former should be used for the activation of hindered species, since the latter may lead to the formation of guanidino derivatives.
• Peptaibolin analogues by incorporation of α,α-dialkylglycines: synthesis and study of their membrane permeating ability
  作者：Vânia I.B. Castro、Carina M. Carvalho、Rui D.V. Fernandes、Sílvia M.M.A. Pereira-Lima、Elisabete M.S. Castanheira、Susana P.G. Costa

  DOI：10.1016/j.tet.2015.12.079

  日期：2016.2

  Analogues of Peptaibolin, a peptaibol with antibiotic activity, incorporating alpha,alpha-dialkylglycines (Deg, Dpg, and Ac(6)c) at selected positions were synthesised by MW-SPPS and fully characterized. A control analogue incorporating L-alanine was also prepared. The native peptide and the analogues were studied by fluorescence spectroscopy for their membrane permeating activity. Small unilamellar vesicles (SUVs) of egg phosphatidylcholine/cholesterol (70:30) containing an encapsulated fluorescence probe (6-carboxyfluorescein) were used as membrane models. The assays of carboxyfluorescein release from SUVs upon peptide addition showed that Peptaibolin-Dpg and Peptaibolin-Ac(6)c are the most active peptides. These results indicate that the structure of the alpha,alpha-diallcylglycines is crucial for the membrane permeating ability of these Peptaibolin analogues. (C) 2016 Elsevier Ltd. All rights reserved.
• Thermodynamic and Structural Impact of α,α-Dialkylated Residue Incorporation in a β-Hairpin Peptide
  作者：Megan A. Karnes、Shelby L. Schettler、Halina M. Werner、Alana F. Kurz、W. Seth Horne、George A. Lengyel

  DOI：10.1021/acs.orglett.6b01936

  日期：2016.8.5

  Peptides containing alpha,alpha-dialkylated alpha-amino acids, owing to their ability to disrupt aggregation of beta-amyloid proteins, have therapeutic potential in the treatment of neurodegenerative diseases. Thermodynamic and structural analyses are reported for a series of beta-hairpin peptides containing alpha,alpha-dialkylated alpha-amino acids with varying side chain lengths. The results of these experiments show that alpha,alpha-dialkylated alpha-amino acids with side-chain lengths longer than one carbon unit are tolerated in a beta-hairpin, although at a moderate cost to folded stability.
• α,α-Cyclic aminoacids as useful scaffolds for the preparation of hNK2 receptor antagonists
  作者：Alessandro Sisto、Maria Altamura、Franco Cardinali、Piero D’Andrea、Cristina Rossi、Daniela Fattori

  DOI：10.1016/j.bmcl.2007.06.053

  日期：2007.9

  MEN 15596 is a small molecule, potent and selective antagonist of NK2 receptor, possessing high affinity and potency at the guinea-pig and human receptors whose pharmacological characterization has been recently published. Here we report how the corresponding class of compounds was derived from a tri-peptide library and the first optimization round to improve both in vitro activity and physicochemical properties. (c) 2007 Elsevier Ltd. All rights reserved.