N-tert-butoxycarbonyl-L-leucylacetic acid

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: N-tert-butoxycarbonyl-L-leucylacetic acid
• 英文别名: (4S)-6-methyl-4-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxoheptanoic acid
• 化学式: C₁₃H₂₃NO₅
• 分子量: 273.329
• InChiKey: MFOXUDDHQTWQBA-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  92.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-tert-butoxycarbonyl-L-leucylacetic acid 以 三氟乙酸 为溶剂， 反应 1.0h， 生成 L-亮氨酸
  参考文献：
  名称：

  Isolation and Structures of Nostopeptolides A1, A2 and A3 from the Cyanobacterium Nostoc sp. GSV224

  摘要：

  The isolation and total structure determinations of nostopeptolides A1 (1), A2 (2) and A3 (3) are described. These cyclic depsipeptides, which are devoid of cytotoxic, antifungal and inhibition of protease activities, are characteristic constituents of the cryptophycin-producing cyanobacterium Nostoc sp. GSV224. Structure elucidation by NMR analysis was made more challenging by the existence of each nostopeptolide in three conformations. One-dimensional TOCSY experiments proved to be very useful in isolating and identifying the nine amino acid residues and the butyryl group in each compound. The absolute stereochemistries of 1-3 were determined by comparing the amino acids in the acid hydrolyzates directly with authentic standards. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00764-x
• 作为产物：
  描述：

  (4S)-4-<(tert-butyloxycarbonyl)amino>-6-methyl-3-oxoheptanoic acid ethyl ester 在 sodium hydroxide 作用下， 以 乙二醇二甲醚 为溶剂， 反应 2.0h， 以0.35 g的产率得到N-tert-butoxycarbonyl-L-leucylacetic acid
  参考文献：
  名称：

  Isolation and Structures of Nostopeptolides A1, A2 and A3 from the Cyanobacterium Nostoc sp. GSV224

  摘要：

  The isolation and total structure determinations of nostopeptolides A1 (1), A2 (2) and A3 (3) are described. These cyclic depsipeptides, which are devoid of cytotoxic, antifungal and inhibition of protease activities, are characteristic constituents of the cryptophycin-producing cyanobacterium Nostoc sp. GSV224. Structure elucidation by NMR analysis was made more challenging by the existence of each nostopeptolide in three conformations. One-dimensional TOCSY experiments proved to be very useful in isolating and identifying the nine amino acid residues and the butyryl group in each compound. The absolute stereochemistries of 1-3 were determined by comparing the amino acids in the acid hydrolyzates directly with authentic standards. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00764-x

文献信息

• Chemoenzymatic Synthesis of Novel Cytotoxic Epoxyketones Using the Eponemycin Biosynthetic Enzyme EpnF
  作者：Broderick C. Corless、Raphael Geißen、Nicholas A. Prescott、Yael David、David A. Scheinberg、Derek S. Tan

  DOI：10.1021/acschembio.3c00080

  日期：2023.6.16

  Eponemycin is an α,β-epoxyketone natural product that inhibits the proteasome via covalent interaction of the epoxyketone warhead with catalytic N-terminal threonine residues. The epoxyketone warhead is biosynthesized from a β-ketoacid substrate by EpnF, a recently identified flavin-dependent acyl-CoA dehydrogenase-like enyzme. Herein, we report biochemical characterization of EpnF kinetics and substrate

  Eponemycin 是一种 α,β-环氧酮天然产物，通过环氧酮弹头与催化 N 末端苏氨酸残基的共价相互作用来抑制蛋白酶体。环氧酮弹头是由 EpnF 从 β-酮酸底物生物合成的，EpnF 是最近发现的黄素依赖性酰基辅酶 A 脱氢酶样酶。在此，我们使用一系列合成 β-酮酸底物报告了 EpnF 动力学和底物范围的生化表征。这些研究表明，环氧化物的形成可能发生在生物合成途径中的其他定制反应之前，并导致鉴定出具有有效抗癌活性的新型环氧酮类似物。
• US4816598A
  申请人：——

  公开号：US4816598A

  公开（公告）日：1989-03-28
• Isolation and Structures of Nostopeptolides A1, A2 and A3 from the Cyanobacterium Nostoc sp. GSV224
  作者：Trimurtulu Golakoti、Wesley Y. Yoshida、Sreedhara Chaganty、Richard E. Moore

  DOI：10.1016/s0040-4020(00)00764-x

  日期：2000.11

  The isolation and total structure determinations of nostopeptolides A1 (1), A2 (2) and A3 (3) are described. These cyclic depsipeptides, which are devoid of cytotoxic, antifungal and inhibition of protease activities, are characteristic constituents of the cryptophycin-producing cyanobacterium Nostoc sp. GSV224. Structure elucidation by NMR analysis was made more challenging by the existence of each nostopeptolide in three conformations. One-dimensional TOCSY experiments proved to be very useful in isolating and identifying the nine amino acid residues and the butyryl group in each compound. The absolute stereochemistries of 1-3 were determined by comparing the amino acids in the acid hydrolyzates directly with authentic standards. (C) 2000 Elsevier Science Ltd. All rights reserved.