Z-Leu-Ala-OBu | 53481-48-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Z-Leu-Ala-OBu
• 英文别名: Z-Leu-Ala-OtBu；Z-Leu-Ala-OBu^t；(S)-tert-butyl 2-((S)-2-(benzyloxycarbonylamino)-4-methylpentanamido)propanoate；tert-butyl (2S)-2-[[(2S)-4-methyl-2-(phenylmethoxycarbonylamino)pentanoyl]amino]propanoate
• CAS: 53481-48-4
• 化学式: C₂₁H₃₂N₂O₅
• 分子量: 392.495
• InChiKey: YVQTUZHIYYECSM-RDJZCZTQSA-N

物化性质

• 熔点：
  70-72 °C
• 沸点：
  541.8±40.0 °C(Predicted)
• 密度：
  1.091±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Z-Leu-Ala-OBu 在 钯 氢气 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 Z-Ala-Leu-Ala-OtBu
  参考文献：
  名称：

  Saito, Kazuki; Higashijima, Tsutomu; Miyazawa, Tatsuo, Chemical and pharmaceutical bulletin, 1984, vol. 32, # 6, p. 2187 - 2193

  摘要：

  DOI：
• 作为产物：
  描述：

  (S)-2-(benzyloxycarbonylamino)propionic acid tert-butyl ester 在 钯 氢气 、 N,N'-二环己基碳二亚胺 、 HONB 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 15.0h， 生成 Z-Leu-Ala-OBu
  参考文献：
  名称：

  Saito, Kazuki; Higashijima, Tsutomu; Miyazawa, Tatsuo, Chemical and pharmaceutical bulletin, 1984, vol. 32, # 6, p. 2187 - 2193

  摘要：

  DOI：

文献信息

• 1-Ethyl 2-Halopyridinium Salts, Highly Efficient Coupling Reagents for Hindered Peptide Synthesis both in Solution and the Solid-Phase
  作者：Peng Li、Jie-Cheng Xu

  DOI：10.1016/s0040-4020(00)00657-8

  日期：2000.10

  proved to be very effective for the synthesis of hindered peptides containing N-methylated or Cα,Cα-dialkylated amino acid residues. HPLC monitoring of model reactions indicated that these pyridinium salts demonstrated higher reactivities, lower racemization than the commonly used halogenated uronium and phosphonium salts. The efficiency of these pyridinium type coupling reagents was further proved by the

  1-乙基-2-卤代吡啶鎓盐，BEP，FEP，BEPH和FEPH，合成并证明是含有受阻的肽的合成是非常有效的Ñ甲基化的或Ç α，Ç α-二烷基化的氨基酸残基。HPLC对模型反应的监测表明，与通常使用的卤化铀盐和phoSPho盐相比，这些吡啶鎓盐具有更高的反应活性和更低的消旋性。通过合成一系列受阻的寡肽和活性酯，具有良好的收率和方便的后处理，进一步证明了这些吡啶鎓类偶联剂的效率。使用这些吡啶鎓盐还成功合成了环孢菌素A（CsA）的8-11四肽片段和Dolastatin 15的五肽部分。这些吡啶鎓类偶联剂对SPPS的效率还通过CsA的极受阻碍的8-11肽段和CsO的线性十一肽的固相合成证明。1 H NMR，IR和HPLC。提出主要的反应性中间体是N-保护的氨基酸或肽的相应的酰卤和酰氧基吡啶鎓盐。
• Application of desymmetrization protocol for the formal total synthesis of emericellamide B
  作者：Debendra K. Mohapatra、Sk. Samad Hossain、Santu Dhara、J.S. Yadav

  DOI：10.1016/j.tetlet.2010.04.015

  日期：2010.6

  A highly convergent formal total synthesis of emericellamide B, a 19-membered antibacterial depsipeptide is described. The key feature of the strategy is the generation of four stereogenic centers from a bicyclic precursor via desymmetrization technique and utilization for emericellamide B and related natural product synthesis. (C) 2010 Elsevier Ltd. All tights reserved.
• Synthesis and antiviral activity of VP1 fragments of the aphthous fever virus
  作者：S. S. Rybakov、N. V. Belyaeva、I. A. Pronin、A. V. Pavlov、A. A. Lugovskoi、V. N. Petrov

  DOI：10.1007/bf02464250

  日期：1997.12
• Exploring Structural Determinants of Inhibitor Affinity and Selectivity in Complexes with Histone Deacetylase 6
  作者：Jeremy D. Osko、Nicholas J. Porter、Poli Adi Narayana Reddy、You-Cai Xiao、Johanna Rokka、Manfred Jung、Jacob M. Hooker、Joseph M. Salvino、David W. Christianson

  DOI：10.1021/acs.jmedchem.9b01540

  日期：2020.1.9

  Inhibition of histone deacetylase 6 (HDAC6) has emerged as a promising therapeutic strategy for the treatment of cancer, chemotherapy-induced peripheral neuropathy, and neurodegenerative disease. The recent X-ray crystal structure determination of HDAC6 enables an understanding of structural features directing affinity and selectivity in the active site. Here, we present the X-ray crystal structures of five HDAC6-inhibitor complexes that illuminate key molecular features of the inhibitor linker and capping groups that facilitate and differentiate binding to HDAC6. In particular, aromatic and heteroaromatic linkers nestle within an aromatic cleft defined by F583 and F643, and different aromatic linkers direct the capping group toward shallow pockets defined by the L1 loop, the L2 loop, or somewhere in between these pockets. These results expand our understanding of factors contributing to the selective inhibition of HDAC6, particularly regarding interactions that can be targeted in the region of the L2 pocket.