(3SR,4S)-benzyl N-Boc-4-amino-2,2-dimethyl-3-hydroxypentanoate | 637778-83-7

• 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: (3SR,4S)-benzyl N-Boc-4-amino-2,2-dimethyl-3-hydroxypentanoate
• 英文别名: (4S)-N-Boc-4-amino-2,2-dimethyl-3-hydroxy-pentanoic acid benzyl ester；benzyl (4S)-3-hydroxy-2,2-dimethyl-4-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate
• CAS: 637778-83-7
• 化学式: C₁₉H₂₉NO₅
• 分子量: 351.443
• InChiKey: WUQAHCSASMXUJK-CFMCSPIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3SR,4S)-benzyl N-Boc-4-amino-2,2-dimethyl-3-hydroxypentanoate 在 5%-palladium/activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 18.0h， 生成 (3SR,4S)-N-Boc-4-amino-2,2-dimethyl-3-hydroxypentanoic acid
  参考文献：
  名称：

  Cyclic Depsipeptides, Grassypeptolides D and E and Ibu-epidemethoxylyngbyastatin 3, from a Red Sea Leptolyngbya Cyanobacterium

  摘要：

  Two new grassypeptolides and a lyngbyastatin analogue, together with the known dolastatin 12, have been isolated from field collections and laboratory cultures of the marine cyanobacterium Leptolyngbya sp. collected from the SS Thistlegorm shipwreck in the Red Sea. The overall stereostructures of grassypeptolides D (1) and E (2) and Ibu-epidemethoxylyngbyastatin 3 (3) were determined by a combination of 1D and 2D NMR experiments, MS analysis, Marfey's methodology, and HPLC-MS. Compounds 1 and 2 contain 2-methyl-3-aminobutyric acid and 2-aminobutyric acid, while biosynthetically distinct 3 contains 3-amino-2-methylhexanoic acid and the beta-keto amino acid 4-amino-2,2-dimethyl-3-oxopentanoic acid (Ibu). Grassypeptolides D (1) and E (2) showed significant cytotoxicity to HeLa (IC50 = 335 and 192 nM, respectively) and mouse neuro-2a blastoma cells (IC50 = 599 and 407 nM, respectively), in contrast to Ibu-epidemethoxylyngbyastatin 3 (neuro-2a cells, IC50 > 10 mu M) and dolastatin 12 (neuro-2a cells, IC50 > 1 mu M).

  DOI：

  10.1021/np200270d
• 作为产物：
  描述：

  (4S)-benzyl N-Boc-4-amino-2,2-dimethyl-3-oxopentanoate 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 (3SR,4S)-benzyl N-Boc-4-amino-2,2-dimethyl-3-hydroxypentanoate
  参考文献：
  名称：

  Isolation and Structure Determination of Lyngbyastatin 3, a Lyngbyastatin 1 Homologue from the Marine Cyanobacterium Lyngbya majuscula. Determination of the Configuration of the 4-Amino-2,2-dimethyl-3-oxopentanoic Acid Unit in Majusculamide C, Dolastatin 12, Lyngbyastatin 1, and Lyngbyastatin 3 from Cyanobacteria

  摘要：

  The structure of lyngbyastatin 3 (1), including the configurations of the two unusual amino acid residues, viz., the 3-amino-2-methylhexanoic acid (Amha) and 4-amino-2,2-dimethyl-3-oxopentanoic acid units (Ibu), has been established by chemical degradation. Analysis of the cyanobacterial samples of lyngbyastatin 3 (1), lyngbyastatin 1 (2), and dolastatin 12 (3) demonstrated that they are mixtures of Ibu epimers [R (major) and S (minor)], whereas the structurally related majusculamide C (4) is a single diastereomer having an S-Ibu unit.

  DOI：

  10.1021/np0302145