[(2R,3S)-4-[[(2S)-1-[(2S,4S)-4-hydroxy-2-[(2S)-2-methyl-5-oxo-2H-pyrrole-1-carbonyl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]-methylamino]-3-[[(2S)-4-methyl-2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]pentanoyl]amino]-4-oxobutan-2-yl] acetate | 177607-82-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: [(2R,3S)-4-[[(2S)-1-[(2S,4S)-4-hydroxy-2-[(2S)-2-methyl-5-oxo-2H-pyrrole-1-carbonyl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]-methylamino]-3-[[(2S)-4-methyl-2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]pentanoyl]amino]-4-oxobutan-2-yl] acetate
• CAS: 177607-82-8
• 化学式: C₃₄H₅₅N₅O₁₀
• 分子量: 693.838
• InChiKey: WVRCTGFNFYSHLQ-ISZNMFDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  49
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  183
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  [(2R,3S)-4-[[(2S)-1-[(2S,4S)-4-hydroxy-2-[(2S)-2-methyl-5-oxo-2H-pyrrole-1-carbonyl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]-methylamino]-3-[[(2S)-4-methyl-2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]pentanoyl]amino]-4-oxobutan-2-yl] acetate 在 盐酸 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 Acetic acid (1R,2S)-2-({(S)-1-[(2S,4S)-4-hydroxy-2-((S)-2-methyl-5-oxo-2,5-dihydro-pyrrole-1-carbonyl)-pyrrolidine-1-carbonyl]-2-methyl-propyl}-methyl-carbamoyl)-1-methyl-2-[(S)-4-methyl-2-(methyl-octanoyl-amino)-pentanoylamino]-ethyl ester
  参考文献：
  名称：

  Developing microcolin A analogs as biological probes

  摘要：

  Three microcolin A and B analogs have been synthesized. Their biological activity profiles were evaluated against several cell lines, revealing the existence of a structural determinant whose role in mediating the antiproliferative effect of the microcolins has heretofore gone unrecognized. While previously described as potent immunosuppressive natural products, we found that these microcolin analogs possessed no selective cytotoxicity when comparing immune cell versus nonimmune cell proliferation. In addition, the amino-terminus of microcolin A has been modified to incorporate a biotinylated polyethylene glycol linker. The biological activity of this biotinylated microcolin A analog was determined. This affinity reagent was shown to retain limited biological activity and thus can serve as a useful probe for elucidating the mechanism of action of microcolin A. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.020
• 作为产物：
  描述：

  (2S,4S)-1-benzyl 2-methyl 4-(tert-butyldimethylsilyloxy)pyrrolidine-1,2-dicarboxylate 在 palladium on activated charcoal 盐酸 、 lithium hydroxide 、 正丁基锂 、 氢气 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 45.0h， 生成 [(2R,3S)-4-[[(2S)-1-[(2S,4S)-4-hydroxy-2-[(2S)-2-methyl-5-oxo-2H-pyrrole-1-carbonyl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]-methylamino]-3-[[(2S)-4-methyl-2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]pentanoyl]amino]-4-oxobutan-2-yl] acetate
  参考文献：
  名称：

  Developing microcolin A analogs as biological probes

  摘要：

  Three microcolin A and B analogs have been synthesized. Their biological activity profiles were evaluated against several cell lines, revealing the existence of a structural determinant whose role in mediating the antiproliferative effect of the microcolins has heretofore gone unrecognized. While previously described as potent immunosuppressive natural products, we found that these microcolin analogs possessed no selective cytotoxicity when comparing immune cell versus nonimmune cell proliferation. In addition, the amino-terminus of microcolin A has been modified to incorporate a biotinylated polyethylene glycol linker. The biological activity of this biotinylated microcolin A analog was determined. This affinity reagent was shown to retain limited biological activity and thus can serve as a useful probe for elucidating the mechanism of action of microcolin A. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.020

文献信息

• Developing microcolin A analogs as biological probes
  作者：Amit K. Mandal、John Hines、Kouji Kuramochi、Craig M. Crews

  DOI：10.1016/j.bmcl.2005.06.020

  日期：2005.9

  Three microcolin A and B analogs have been synthesized. Their biological activity profiles were evaluated against several cell lines, revealing the existence of a structural determinant whose role in mediating the antiproliferative effect of the microcolins has heretofore gone unrecognized. While previously described as potent immunosuppressive natural products, we found that these microcolin analogs possessed no selective cytotoxicity when comparing immune cell versus nonimmune cell proliferation. In addition, the amino-terminus of microcolin A has been modified to incorporate a biotinylated polyethylene glycol linker. The biological activity of this biotinylated microcolin A analog was determined. This affinity reagent was shown to retain limited biological activity and thus can serve as a useful probe for elucidating the mechanism of action of microcolin A. (c) 2005 Elsevier Ltd. All rights reserved.