N^α-(9-fluorenylmethoxycarbonyl)-2,2-diisobutylglycine | 397299-36-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: N^α-(9-fluorenylmethoxycarbonyl)-2,2-diisobutylglycine
• 英文别名: N-(9-fluorenylmethyloxycarbonyl)-α,α-diisobutylglycine；Fmoc-Dibg-OH；2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-methyl-2-(2-methylpropyl)pentanoic acid
• CAS: 397299-36-4
• 化学式: C₂₅H₃₁NO₄
• 分子量: 409.525
• InChiKey: ODHZAQGXWXKCEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 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-alpha-芴甲氧羰基-N-epsilon-叔丁氧羰基-L-赖氨酸 、 (Fmc-Val)2O 、 N^α-(9-fluorenylmethoxycarbonyl)-2,2-dibenzylglycine 、 N^α-(9-fluorenylmethoxycarbonyl)-2,2-diisobutylglycine 、 alkaline earth salt of/the/ methylsulfuric acid 生成 N-[(2S)-1-[[1-[[(2S)-1-[4-[[(2S)-6-amino-1-[[(2S)-6-amino-1-[[(2S)-6-amino-1-[[(2S)-6-amino-1-[[(2S)-6-amino-1-[[(2S)-1,6-diamino-1-oxohexan-2-yl]amino]-1-oxohexan-2-yl]amino]-1-oxohexan-2-yl]amino]-1-oxohexan-2-yl]amino]-1-oxohexan-2-yl]amino]-1-oxohexan-2-yl]carbamoyl]heptan-4-ylamino]-1-oxo-3-phenylpropan-2-yl]amino]-2-benzyl-1-oxo-3-phenylpropan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]-2-[[(2S)-2,6-diaminohexanoyl]amino]-4-methyl-2-(2-methylpropyl)pentanamide
  参考文献：
  名称：

  Efficient Acylation of the N-Terminus of Highly Hindered C^α,α-Disubstituted Amino Acids via Amino Acid Symmetrical Anhydrides

  摘要：

  GRAPHICSFmoc amino acid symmetrical anhydrides are efficient and readily available reagents for acylation of the N-terminus of highly hindered C-alpha,C-alpha-dialkylated alpha-amino acids. Comparison of a variety of coupling protocols showed that the symmetrical anhydride method always provided the superior results. This method was successfully applied to the solid-phase synthesis of a peptide containing three alphaalphaAAs at alternating positions.

  DOI：

  10.1021/ol016965k
• 作为产物：
  描述：

  2,2-diisobutylglycine 、 氯甲酸-9-芴基甲酯 在 三甲基氯硅烷 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 28.0h， 以88%的产率得到N^α-(9-fluorenylmethoxycarbonyl)-2,2-diisobutylglycine
  参考文献：
  名称：

  Facile Synthesis of α,α-Diisobutylglycine and Anchoring Its Derivatives onto PAL-PEG-PS Resin

  摘要：

  alpha,alpha-Diisobutylglycine has been synthesized using a Pd-mediated dialkylation of ethyl nitroacetate as a key first step. The free alphaalphaAA is N-alpha-protected and has been applied to the assembly of conformationally constrained peptide analogues. Mixed anhydrides from BOP-Cl and Fmoc-alphaalphaAA-OH are used for anchoring alphaalphaAAs onto a trialkoxybenzyl linker on PEG-PS grafted support, upon which a beta-strand mimic with difficult sequence is assembled in a superior quality.

  DOI：

  10.1021/jo034885j

文献信息

• 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.
• Efficient Acylation of the <i>N</i>-Terminus of Highly Hindered <i>C</i>^α^,^α-Disubstituted Amino Acids via Amino Acid Symmetrical Anhydrides
  作者：Yanwen Fu、Robert P. Hammer

  DOI：10.1021/ol016965k

  日期：2002.1.1

  GRAPHICSFmoc amino acid symmetrical anhydrides are efficient and readily available reagents for acylation of the N-terminus of highly hindered C-alpha,C-alpha-dialkylated alpha-amino acids. Comparison of a variety of coupling protocols showed that the symmetrical anhydride method always provided the superior results. This method was successfully applied to the solid-phase synthesis of a peptide containing three alphaalphaAAs at alternating positions.
• Facile Synthesis of α,α-Diisobutylglycine and Anchoring Its Derivatives onto PAL-PEG-PS Resin
  作者：Yanwen Fu、Marcus A. Etienne、Robert P. Hammer

  DOI：10.1021/jo034885j

  日期：2003.12.1

  alpha,alpha-Diisobutylglycine has been synthesized using a Pd-mediated dialkylation of ethyl nitroacetate as a key first step. The free alphaalphaAA is N-alpha-protected and has been applied to the assembly of conformationally constrained peptide analogues. Mixed anhydrides from BOP-Cl and Fmoc-alphaalphaAA-OH are used for anchoring alphaalphaAAs onto a trialkoxybenzyl linker on PEG-PS grafted support, upon which a beta-strand mimic with difficult sequence is assembled in a superior quality.