Boc-D-Ala-D-Glu(CH2Ph)-NH2 | 63091-91-8

• 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: Boc-D-Ala-D-Glu(CH2Ph)-NH2
• 英文别名: Boc-D-Ala-D-Glu(OBn)(OBn)-NH2；benzyl (4R)-5-amino-4-[[(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]-5-oxopentanoate
• CAS: 63091-91-8
• 化学式: C₂₀H₂₉N₃O₆
• 分子量: 407.467
• InChiKey: GBWLWWKUNXXPCZ-UKRRQHHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  137
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Boc-D-Ala-D-Glu(CH2Ph)-NH2 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 6.0h， 生成 benzyl (4R)-5-amino-5-oxo-4-[((2R)-2-{[5-(1,1,3-trioxo-1,3-dihydro-2H-1,2-benzisothiazol-2-yl)pentanoyl]amino}propanoyl)amino]pentanoate
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel desmuramyldipeptide analogs

  摘要：

  A series of novel desmuramyldipeptides have been designed and synthesized as part of our search for therapeutically useful muramyldipeptide (MOP) analogs. Their immunomodulatory properties were initially assessed in vitro, evaluating their effect on lipopolysaccharide (LPS)-induced cytokine release in THP-1 cells. Following the initial screening, selected compounds were further investigated for immunomodulatory properties using LPS and phorbol 12-myristate 13-acetate (PMA)/ionomycin-stimulated human peripheral blood mononuclear cells. The results confirmed the immunomodulatory properties of some of the synthesized desmuramyldipeptide analogs. Taken together, presented data confirmed the immunostimulatory effect of compound 44, MDP derivative incorporating a pyrido-fused [1,2]-benzisothiazole moiety, while for compounds 32 and 39, indole scaffold-based derivatives of MOP, an immunosuppressive effect was observed. Further studies will be necessary to address their potential therapeutic use as immunomodulatory drugs, both as immunostimulants or anti-inflammatory agents. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.05.042
• 作为产物：
  描述：

  BOC-D-丙氨酸 、 benzyl D-isoglutaminate hydrochloride 在 N-甲基吗啉 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 生成 Boc-D-Ala-D-Glu(CH2Ph)-NH2
  参考文献：
  名称：

  Syntheses of Several Muramyl Peptides in Relation to Chemical Structures of Less Immunoadjuvant Bacterial Cell Walls

  摘要：

  N-acetylmuramyl-l-alanyl-d-isoglutamine 是细菌细胞壁具有免疫佐剂活性所需的最小结构，为了更详细地研究这种活性与化学结构之间的关系，我们合成了 N-acetylmuramyl-l-alanyl-d-isoglutamine 的各种结构类似物。本研究特别制备了与无免疫佐剂活性的特殊细菌细胞壁结构相对应的化合物。本研究还采用了包括制备支链谷氨酰肽在内的几种新方法，合成了结构复杂的氨甲酰肽。通过这项合成研究，我们获得了有关免疫佐剂活性结构要求的新信息。

  DOI：

  10.1246/bcsj.52.1665

文献信息

• Syntheses of Several Muramyl Peptides in Relation to Chemical Structures of Less Immunoadjuvant Bacterial Cell Walls
  作者：Shoichi Kusumoto、Kazuhiro Ikenaka、Tetsuo Shiba

  DOI：10.1246/bcsj.52.1665

  日期：1979.6

  Various structural analogs of N-acetylmuramyl-l-alanyl-d-isoglutamine, which had been shown to be the minimum structure required for the immunoadjuvant activity of bacterial cell walls, were synthesized in order to investigate in more detail the relationship between the activity and chemical structures. Particularly, the compounds of the structures corresponding to the cell walls of special bacteria without immunoadjuvant activity were prepared in this study. Several novel procedures including the preparation of a branched glutamyl peptide were newly exploited to accomplish the syntheses of muramyl peptides with complicated structures. As a result of this synthetic study, new informations were obtained on the structural requirement for the immunoadjucant activity.

  N-acetylmuramyl-l-alanyl-d-isoglutamine 是细菌细胞壁具有免疫佐剂活性所需的最小结构，为了更详细地研究这种活性与化学结构之间的关系，我们合成了 N-acetylmuramyl-l-alanyl-d-isoglutamine 的各种结构类似物。本研究特别制备了与无免疫佐剂活性的特殊细菌细胞壁结构相对应的化合物。本研究还采用了包括制备支链谷氨酰肽在内的几种新方法，合成了结构复杂的氨甲酰肽。通过这项合成研究，我们获得了有关免疫佐剂活性结构要求的新信息。
• Design, synthesis and biological evaluation of novel desmuramyldipeptide analogs
  作者：Žiga Jakopin、Emanuela Corsini、Martina Gobec、Irena Mlinarič-Raščan、Marija Sollner Dolenc

  DOI：10.1016/j.ejmech.2011.05.042

  日期：2011.9

  A series of novel desmuramyldipeptides have been designed and synthesized as part of our search for therapeutically useful muramyldipeptide (MOP) analogs. Their immunomodulatory properties were initially assessed in vitro, evaluating their effect on lipopolysaccharide (LPS)-induced cytokine release in THP-1 cells. Following the initial screening, selected compounds were further investigated for immunomodulatory properties using LPS and phorbol 12-myristate 13-acetate (PMA)/ionomycin-stimulated human peripheral blood mononuclear cells. The results confirmed the immunomodulatory properties of some of the synthesized desmuramyldipeptide analogs. Taken together, presented data confirmed the immunostimulatory effect of compound 44, MDP derivative incorporating a pyrido-fused [1,2]-benzisothiazole moiety, while for compounds 32 and 39, indole scaffold-based derivatives of MOP, an immunosuppressive effect was observed. Further studies will be necessary to address their potential therapeutic use as immunomodulatory drugs, both as immunostimulants or anti-inflammatory agents. (C) 2011 Elsevier Masson SAS. All rights reserved.