N-((1,1-Dimethylethoxy)carbonyl)-β-Ala-O-D-Leu-OH | 55739-21-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-((1,1-Dimethylethoxy)carbonyl)-β-Ala-O-D-Leu-OH
• 英文别名: (2R)-4-methyl-2-[3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyloxy]pentanoic acid
• CAS: 55739-21-4
• 化学式: C₁₄H₂₅NO₆
• 分子量: 303.356
• InChiKey: IEEKUJVTKBHGJJ-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-((1,1-Dimethylethoxy)carbonyl)-β-Ala-O-D-Leu-OH 在 palladium on activated charcoal 4-二甲氨基吡啶 、 二苯基磷酸 、 氢气 、 N,N-二异丙基乙胺 、 bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 48.0h， 生成 leualacin
  参考文献：
  名称：

  Synthesis and evaluation of backbone/amide-modified analogs of leualacin

  摘要：

  Leualacin (1), a cyclic depsi-pentapeptide, and its backbone/amide-modified analogs 2-4 were synthesized. Amide analogue 3 exhibited stronger vasodilatory effects. It also strongly inhibited collagen- and arachidonic acid (AA)induced platelet aggregations with IC(50)s of 0.6 mu M and 2.0 mu M, respectively (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00038-4
• 作为产物：
  描述：

  (R)-2-羟基-4-甲基戊酸 在 palladium on activated charcoal 4-二甲氨基吡啶 、 异丙烯基氯甲酸酯 、 碘苯二乙酸 、 氢气 、 碘 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 8.0h， 生成 N-((1,1-Dimethylethoxy)carbonyl)-β-Ala-O-D-Leu-OH
  参考文献：
  名称：

  Total Synthesis of the Cyclic Depsipeptide Leualacin

  摘要：

  The fungal metabolite leualacin (1), a potent calcium channel antagonist, was synthesized in 15 steps from commercially available amino acids in 25% overall yield using standard solution methods. The synthesis is general and thus would accommodate the incorporation of amino acid replacements as well as the inclusion of peptide mimics and isosteres.

  DOI：

  10.1021/jo00124a019

文献信息

• Total Synthesis of the Cyclic Depsipeptide Leualacin
  作者：Kevin L. McLaren

  DOI：10.1021/jo00124a019

  日期：1995.9

  The fungal metabolite leualacin (1), a potent calcium channel antagonist, was synthesized in 15 steps from commercially available amino acids in 25% overall yield using standard solution methods. The synthesis is general and thus would accommodate the incorporation of amino acid replacements as well as the inclusion of peptide mimics and isosteres.
• Synthesis of a cyclohexadepsipeptide, protodestruxin
  作者：Sannamu Lee、Nobuo izumiya、Akinori Suzuki、Saburo Tamura

  DOI：10.1016/s0040-4039(00)72010-7

  日期：1975.1
• Synthesis and evaluation of backbone/amide-modified analogs of leualacin
  作者：Ming-Kuan Hu、Fu-Chu Yang、Chi-Cheun Chou、Mao-Hsiung Yen

  DOI：10.1016/s0960-894x(99)00038-4

  日期：1999.2

  Leualacin (1), a cyclic depsi-pentapeptide, and its backbone/amide-modified analogs 2-4 were synthesized. Amide analogue 3 exhibited stronger vasodilatory effects. It also strongly inhibited collagen- and arachidonic acid (AA)induced platelet aggregations with IC(50)s of 0.6 mu M and 2.0 mu M, respectively (C) 1999 Elsevier Science Ltd. All rights reserved.