FMOC-L-2-氨基辛二酸 | 218457-76-2

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - FMOC-氨基酸
• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: FMOC-L-2-氨基辛二酸
• 英文名称: Fmoc-L-Asu-OH
• 英文别名: Fmoc-L-alpha-aminosuberic acid；(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)octanedioic acid
• CAS: 218457-76-2
• 化学式: C₂₃H₂₅NO₆
• 分子量: 411.455
• InChiKey: IMAOCPQKEUWDNC-FQEVSTJZSA-N

物化性质

• 沸点：
  670.9±55.0 °C(Predicted)
• 密度：
  1.286±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  6

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  FMOC-L-2-氨基辛二酸 、 邻苯二胺 在 trityl chloride resin 、 N,N-二异丙基乙胺 、 N-羟基-7-氮杂苯并三氮唑 、 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 (9H-fluoren-9-yl)methyl (S)-(1,8-bis((2-aminophenyl)amino)-1,8-dioxooctan-2-yl)carbamate
  参考文献：
  名称：

  Design and synthesis of novel hybrid benzamide–peptide histone deacetylase inhibitors

  摘要：

  We designed and synthesized a series of novel hybrid histone deacetylase inhibitors based on conjugation of benzamide-type inhibitors with either linear or cyclic peptides. Linear tetrapeptides (compounds 13 and 14), cyclic tetrapeptides (compounds 1 and 11), and heptanediamide-peptide conjugates (compounds 10, 12, 15 and 16) were synthesized through on-resin solid-phase peptide synthesis (SPPS). All compounds were found to be moderate HDAC1 and HDAC3 inhibitors, with IC50 values ranging from 1.3 mu M to 532 mu M. Interestingly, compound 15 showed 19-fold selectivity for HDAC3 versus HDAC1. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.085
• 作为产物：
  描述：

  (S)-2-氨基辛二酸 、 9-芴甲基-N-琥珀酰亚胺基碳酸酯 在 碳酸氢钠 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 20.0h， 以100%的产率得到FMOC-L-2-氨基辛二酸
  参考文献：
  名称：

  Solid phase synthesis of hydroxamate peptides for histone deacetylase inhibition

  摘要：

  An orthogonal protecting group strategy was devised to synthesize hydroxamic acid containing peptides for biomimetic histone deacetylase (HDAC) inhibition. The basic building block was a protected aminosuberic acid (Asu) derivative bearing a protected hydroxamate in the side-chain, related closely to HDAC inhibitors that are transition-state analogs of acetyllysine. These inhibitors include suberoylanilide hydroxamic acid (SAHA), currently being used to treat a variety of human cancers. This strategy was employed to synthesize a series of nonameric peptides related to actual HDAC substrates, derived from known sites of acetylation/deacetylation on the N-terminal tails of the histone core proteins H2A, H2B, H3, and H4. In each case the lysine residue was replaced by a hydroxamate-bearing side chain, to mimic the endogenous site of deacetylation. Mass spectrometry and high performance liquid chromatography (HPLC) confirmed the success of automated solid-phase synthesis. These results suggest facile synthesis of a new class of HDAC inhibitors that may have enhanced selectivity for specific HDAC isoforms. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.10.113