(2R,3R)-3-(BOC-氨基)-2-羟基-5-甲基己酸 | 73397-26-9

• 物质功能分类: 生物化工 - 生化试剂 - 氨基酸
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: (2R,3R)-3-(BOC-氨基)-2-羟基-5-甲基己酸
• 中文别名: Boc-(2R,3R)-3-氨基-2-羟基-5-甲基己酸；(2R,3R)-3-(Boc-氨基)-2-羟基-5-甲基己酸
• 英文名称: (2R,3R)-3-<<(tert-Butyloxy)carbonyl>amino>-2-hydroxy-5-methylhexanoic Acid
• 英文别名: (2R,3R)-3-{[(tert-Butyloxy)carbonyl]amino}-2-hydroxy-5-methylhexanoic Acid；(2R,3R)-3-((tert-Butoxycarbonyl)amino)-2-hydroxy-5-methylhexanoic acid；(2R,3R)-2-hydroxy-5-methyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoic acid
• CAS: 73397-26-9
• 化学式: C₁₂H₂₃NO₅
• mdl: MFCD00058525
• 分子量: 261.318
• InChiKey: DJZCWTDKDFJARG-RKDXNWHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.833
• 拓扑面积：
  95.9
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2924199090

反应信息

• 作为反应物：
  描述：

  L-亮氨酸甲酯盐酸盐 、 (2R,3R)-3-(BOC-氨基)-2-羟基-5-甲基己酸 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 (2R,3R)-<3-<<(tert-Butyloxy)carbonyl>amino>-2-hydroxy-5-methylhexanoyl>-L-leucine Methyl Ester
  参考文献：
  名称：

  Synthesis of (2S,3R)-3-amino-2-hydroxy-5-methylhexanoic acid derivatives. Application to the synthesis of amastatin, an inhibitor of aminopeptidases

  摘要：

  DOI：

  10.1021/jo01300a004
• 作为产物：
  描述：

  benzyl ((1S,2S)-1-cyano-1-hydroxy-4-methylpentan-2-yl)carbamate 在 盐酸 、 sodium hydroxide 、 三乙胺 作用下， 以 1,4-二氧六环 、 乙醚 、 水 为溶剂， 反应 13.0h， 生成 (2R,3R)-3-(BOC-氨基)-2-羟基-5-甲基己酸
  参考文献：
  名称：

  Synthesis of (2S,3R)-3-amino-2-hydroxy-5-methylhexanoic acid derivatives. Application to the synthesis of amastatin, an inhibitor of aminopeptidases

  摘要：

  DOI：

  10.1021/jo01300a004

文献信息

• Synthesis of New (−)-Bestatin-Based Inhibitor Libraries Reveals a Novel Binding Mode in the S1 Pocket of the Essential Malaria M1 Metalloaminopeptidase
  作者：Geetha Velmourougane、Michael B. Harbut、Seema Dalal、Sheena McGowan、Christine A. Oellig、Nataline Meinhardt、James C. Whisstock、Michael Klemba、Doron C. Greenbaum

  DOI：10.1021/jm101227t

  日期：2011.3.24

  The malarial PfA-M1 metalloaminopeptidase is considered a putative drug target. The natural product dipeptide mimetic, bestatin, is a potent inhibitor of PfA-M1. Herein we present a new, efficient, and high-yielding protocol for the synthesis of bestatin derivatives from natural and unnatural N-Boc-D-amino acids. A diverse library of bestatin derivatives was synthesized with variants at the side chain of either the alpha-hydroxy-beta-amino acid (P1) or the adjacent natural a-amino add (P1'). Surprisingly, we found that extended aromatic side chains at the P1 position resulted in potent inhibition against PfA-M1. To understand these data, we determined the X-ray cocrystal structures of PfA-M1 with two derivatives having either a Tyr(OMe) 15 or Tyr(OBz1) 16 at the 131 position and observed substantial inhibitor-induced rearrangement of the primary loop within the PEA-M1 pocket that interacts with the PI side chain. Our data provide important insights for the rational design of more potent and selective inhibitors of this enzyme that may eventually lead to new therapies for malaria.
• Synthesis of (2S,3R)-3-amino-2-hydroxy-5-methylhexanoic acid derivatives. Application to the synthesis of amastatin, an inhibitor of aminopeptidases
  作者：Daniel H. Rich、Byung Jo Moon、Amrit S. Boparai

  DOI：10.1021/jo01300a004

  日期：1980.6