(R)-2-(N-tert-butoxycarbonylamino)-2-(9-fluorenyl)acetic acid | 915750-96-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (R)-2-(N-tert-butoxycarbonylamino)-2-(9-fluorenyl)acetic acid
• 英文别名: N-Boc-D-fluorenylglycine；N-Boc-D-Flg-OH；(2R)-2-(9H-fluoren-9-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid
• CAS: 915750-96-8
• 化学式: C₂₀H₂₁NO₄
• 分子量: 339.391
• InChiKey: GSODHVQZXQVIPW-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  Fmoc-Ala-Wang resin 、 (R)-2-(N-tert-butoxycarbonylamino)-2-(9-fluorenyl)acetic acid 在 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Therapeutic Index of Gramicidin S is Strongly Modulated by d-Phenylalanine Analogues at the β-Turn

  摘要：

  Analogues of the cationic antimicrobial peptide gramicidin S (GS), cyclo(Val-Orn-Leu-D-Phe-Pro)(2), with D-Phe residues replaced by different (restricted mobility, mostly) surrogates have been synthesized and used in SAR studies against several pathogenic bacteria. While all D-Phe substitutions are shown by NMR to preserve the overall beta-sheet conformation, they entail subtle structural alterations that lead to significant modifications in biological activity. In particular, the analogue incorporating D-Tic (1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid) shows a modest but significant increase in therapeutic index, mostly due to a sharp decrease in hemolytic effect. The fact that NMR data show a shortened distance between the D-Tic aromatic ring and the Orn delta-amino group may help explain the improved antibiotic profile of this analogue.

  DOI：

  10.1021/jm800886n
• 作为产物：
  描述：

  benzyl (R)-2-(N-tert-butoxycarbonylamino)-2-(9-fluorenyl)acetate 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 8.0h， 以100%的产率得到(R)-2-(N-tert-butoxycarbonylamino)-2-(9-fluorenyl)acetic acid
  参考文献：
  名称：

  Synthesis of enantiomerically pure β,β-diphenylalanine (Dip) and fluorenylglycine (Flg)

  摘要：

  A new strategy for the preparation of both enantiomers of two phenylalanine analogues, beta,beta-diphenylalanine and fluorenylglycine, has been developed. The combination of a high yielding racemic synthesis and a very efficient resolution procedure has provided significant amounts of each amino acid in enantiomerically pure form and suitably protected for use in peptide synthesis. This methodology can be easily applied to the preparation of larger quantities of enantiopure compounds. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.08.007