FMOC-O-三苯甲基-D-高丝氨酸 | 257886-01-4

• 物质功能分类: 生物化工 - 氨基酸及其衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 中文名称: FMOC-O-三苯甲基-D-高丝氨酸
• 中文别名: N-[(9H-芴-9-基甲氧基)羰基]-O-三苯甲基-D-高丝氨酸
• 英文名称: Fmoc-D-Homoser(Trt)-OH
• 英文别名: Fmoc-D-Hse(Trt)-OH；(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-trityloxybutanoic acid
• CAS: 257886-01-4
• 化学式: C₃₈H₃₃NO₅
• 分子量: 583.684
• InChiKey: QUTREFXHXPNEJN-PGUFJCEWSA-N

物化性质

• 沸点：
  767.5±60.0 °C(Predicted)
• 密度：
  1.242±0.06 g/cm3(Predicted)
• 稳定性/保质期：

  在指定条件下稳定，远离氧化物。

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  44
• 可旋转键数：
  12
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  FMOC-O-三苯甲基-D-高丝氨酸 、 alkaline earth salt of/the/ methylsulfuric 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-) 、 三异丙基硅烷 、 三氟乙酸 、 哌啶 作用下， 以 N,N-二甲基甲酰胺 、 水 为溶剂， 反应 4.0h， 生成 (R)-2-Amino-4-hydroxy-N-(2-hydroxy-ethyl)-butyramide
  参考文献：
  名称：

  l-Homoserylaminoethanol, a novel dipeptide alcohol inhibitor of eukaryotic DNA polymerase ε from a plant cultured cells, Nicotina tabacum L.

  摘要：

  We found a novel inhibitor specific to eukaryotic DNA polymerase epsilon (pol epsilon) from plant cultured cells, Nicotina tabacum L. The compound (compound 1) was a dipeptide alcohol, L-homoserylaminoethanol. The 50% inhibition of pol epsilon activity by the compound was 43.6 mug/mL, and it had almost no effect on the activities of the other eukaryotic DNA polymerases such as alpha, beta, gamma and delta, prokaryotic DNA polymerases, nor DNA metabolic enzymes such as human telomerase, human immunodeficiency virus type 1 reverse transcriptase, T7 RNA polymerase, human DNA topoisomerase I and II, T4 polynucleotide kinase and bovine deoxyribonuclease I. Kinetic studies showed that inhibition of pol epsilon by the compound was non-competitive with respect to both template-primer DNA and nucleotide substrate. We succeeded in chemically synthesizing the stereoisomers, L-homoserylaminoethanol and D-homoserylaminoethanol, and found both were effective to the same extent. The IC50 values of L- and D-homoserylaminoethanols for pot epsilon were 42.0 and 41.5 mug/mL, respectively. This represents the second discovery of a pol epsilon-specific inhibitor, and the first report on a water-soluble peptide-like compound as the inhibitor, which is required in biochemical studies of pol epsilon. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.12.030

文献信息

• Rapid, Structure-Based Exploration of Pipecolic Acid Amides as Novel Selective Antagonists of the FK506-Binding Protein 51
  作者：Steffen Gaali、Xixi Feng、Andreas Hähle、Claudia Sippel、Andreas Bracher、Felix Hausch

  DOI：10.1021/acs.jmedchem.5b01355

  日期：2016.3.24

  However, drug-like parameters for these ligands remained unfavorable. In the present study, we replaced the potentially labile pipecolic ester group of previous FKBP51 ligands by various low molecular weight amides. This resulted in the first series of pipecolic acid amides, which had much lower molecular weights without affecting FKBP51 selectivity. We discovered a geminally substituted cyclopentyl

  FK506结合蛋白51（FKBP51）是压力激素受体的关键调节剂，并且是与压力相关的疾病的既定危险因素。FKBP51的药物开发受到结构相似但功能相反的同系物FKBP52的破坏。FKBP51和FKBP52之间的高选择性可以通过稳定最近发现的FKBP51有利构象的配体来实现。然而，这些配体的药物样参数仍然是不利的。在本研究中，我们用各种低分子量酰胺取代了以前的FKBP51配体的潜在不稳定的胡椒酸酯基。这产生了第一系列的胡椒酸酰胺，其具有低得多的分子量而不影响FKBP51的选择性。