N-tert-Butyloxycarbonyl-L-leucyl-DL-α-hydroxyglycine allyl ester | 176640-12-3

• 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: N-tert-Butyloxycarbonyl-L-leucyl-DL-α-hydroxyglycine allyl ester
• 英文别名: N-t-butoxycarbonyl-(L)-leucyl-(D,L)-2-hydroxyglycine allyl ester；Boc-Leu-DL-Gly(OH)-Oallyl；prop-2-enyl 2-hydroxy-2-[[(2S)-4-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoyl]amino]acetate
• CAS: 176640-12-3
• 化学式: C₁₆H₂₈N₂O₆
• 分子量: 344.408
• InChiKey: QOGJMAVJPRNJML-AMGKYWFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  24
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-tert-Butyloxycarbonyl-L-leucyl-DL-α-hydroxyglycine allyl ester 在 吡啶 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 N-t-butoxycarbonyl-(L)-leucyl-2-phenylamino-(D,L)-glycine allyl ester
  参考文献：
  名称：

  Synthesis and biological activities of new N-formylated methionyl peptides containing an α-substituted glycine residue

  摘要：

  Small molecular weight peptides related to the well-known chemotactic peptide N-alpha-formyl-methionyl-leucylphenylalanine have been prepared. These compounds were designed to evaluate the requirements in position 3 (phenylalanine). Each analogue containing an alpha-substituted glycine in position 3 was tested for its ability to induce lysosomal enzyme release from cytochalasin B treated human neutrophils. In addition, each analogue was also tested for its ability to antagonize superoxide generation. The results indicate that the analogue N-formyl-methionyl-leucyl-(alpha-anilino)glycine allyl ester is a potent antagonist of superoxide generation. Its ID50's suggest that this compound could be very promising in the field of anti-inflammatory drugs. A hypothetical inhibition mechanism is discussed.

  DOI：

  10.1016/0223-5234(92)90055-6
• 作为产物：
  描述：

  Boc-L-亮氨酰胺 、 allyl 2-oxoacetate 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以44%的产率得到N-tert-Butyloxycarbonyl-L-leucyl-DL-α-hydroxyglycine allyl ester
  参考文献：
  名称：

  Synthesis and chemical reactivity of thiophenoxyphenylalanine bioisosteres, suitable synthons for the design of HIV protease inhibitors

  摘要：

  亚甲基被硫原子取代的苯丙氨酸可能是设计 HIV 蛋白酶抑制剂的有用生物等排体。由于半缩醛胺中间体的化学不稳定性，这些生物等排体必须按照特定的合成路线由α-羟基甘氨酸制备。在本文中，我们报道了磺酰化苯丙氨酸生物等排体2和3的合成，它们代表了肽固相合成的两个原始构建模块。

  DOI：

  10.1039/a907483j

文献信息

• Thiophenoxy peptides: A new class of HIV replication inhibitors
  作者：Valérie Niddam、Michel Camplo、Dung Le Nguyen、Jean-Claude Chermann、Jean-Louis Kraus

  DOI：10.1016/0960-894x(96)00085-6

  日期：1996.3

  A new series of modified peptides inhibitors of HIV is reported. These peptides utilize the isosteric substitution of a methylene group by a sulfur atom in a phenylalanine residue. Two thiophenoxy peptides 9 and 11 inhibit in vitro HIV-1 replication in MT(4) cells with IC50 values of 5 and 10 mu M respectively.
• Synthesis and biological activities of new N-formylated methionyl peptides containing an α-substituted glycine residue
  作者：JL Kraus、G Attardo

  DOI：10.1016/0223-5234(92)90055-6

  日期：1992.1

  Small molecular weight peptides related to the well-known chemotactic peptide N-alpha-formyl-methionyl-leucylphenylalanine have been prepared. These compounds were designed to evaluate the requirements in position 3 (phenylalanine). Each analogue containing an alpha-substituted glycine in position 3 was tested for its ability to induce lysosomal enzyme release from cytochalasin B treated human neutrophils. In addition, each analogue was also tested for its ability to antagonize superoxide generation. The results indicate that the analogue N-formyl-methionyl-leucyl-(alpha-anilino)glycine allyl ester is a potent antagonist of superoxide generation. Its ID50's suggest that this compound could be very promising in the field of anti-inflammatory drugs. A hypothetical inhibition mechanism is discussed.
• Synthesis and chemical reactivity of thiophenoxyphenylalanine bioisosteres, suitable synthons for the design of HIV protease inhibitors
  作者：G. Priem、L. Rocheblave、C. De Michelis、J. Courcambeck、J. L. Kraus

  DOI：10.1039/a907483j

  日期：——

  Phenylalanine in which the methylene group is replaced by a sulfur atom could be a useful bioisostere for the design of HIV-protease inhibitors. Due to the chemical instability of hemiaminal intermediates, these bioisosteres have to be prepared from α-hydroxyglycine following specific synthetic routes. In this paper, we report the synthesis of sulfenylated phenylalanine bioisosteres 2 and 3, which represent two original building-blocks for peptide solid phase synthesis.

  亚甲基被硫原子取代的苯丙氨酸可能是设计 HIV 蛋白酶抑制剂的有用生物等排体。由于半缩醛胺中间体的化学不稳定性，这些生物等排体必须按照特定的合成路线由α-羟基甘氨酸制备。在本文中，我们报道了磺酰化苯丙氨酸生物等排体2和3的合成，它们代表了肽固相合成的两个原始构建模块。