(S)-2-[(R)-2-(2,2-Dimethyl-propionylaminooxy)-4-methyl-pentanoylaminooxy]-3-phenyl-propionic acid tert-butyl ester | 627079-34-9

• 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: (S)-2-[(R)-2-(2,2-Dimethyl-propionylaminooxy)-4-methyl-pentanoylaminooxy]-3-phenyl-propionic acid tert-butyl ester
• CAS: 627079-34-9
• 化学式: C₂₄H₃₈N₂O₆
• 分子量: 450.576
• InChiKey: GAVFNEOUHMPASN-MOPGFXCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  32.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  102.96
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (S)-2-[(R)-2-(2,2-Dimethyl-propionylaminooxy)-4-methyl-pentanoylaminooxy]-3-phenyl-propionic acid tert-butyl ester 在 1-羟基苯并三唑 、 1-[3-(dimethylamino)-propyl]-3-ethylcarbodiimide methiodide 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 (2R)-2-(2,2-dimethylpropanoylamino)oxy-4-methyl-N-[(2S)-1-(2-methylpropylamino)-1-oxo-3-phenylpropan-2-yl]oxypentanamide
  参考文献：
  名称：

  A Reverse Turn Structure Induced by a d,l-α-Aminoxy Acid Dimer

  摘要：

  Our previous work revealed that two adjacent D-a-aminoxy acids could form two homochiral N-O turns, with the backbone folding into an extended helical structure (1.8(8)-helix). Here, we report the conformational studies of linear peptides 3-6, which contain a D,L-alpha-aminoxy acid dimer segment. The NMR and X-ray analysis of 3 showed that it folded into a loop conformation with two heterochiral N-O turns. This loop segment can be used to constrain tetrapeptides 4 and 6 to form a reverse turn structure. H-1 NMR dilution studies, DMSO-d(6) addition studies, and 2D-NOESY data indicated that tetrapeptides 4 and 6 folded into reverse turn conformations featured by a head-to-tail 16-membered-ring intramolecular hydrogen bond. In contrast, tetrapeptide 5 with L-Ala instead of Gly or D-Ala as the N-terminal amino acid could not form the desired reverse turn structure for steric reasons. Quantum mechanics calculations showed that model pentamide 7, with the same substitution pattern of 4, adopted a novel reverse turn conformation featuring two heterochiral N-O turns (each of an 8-membered ring hydrogen bond), a cross-strand 16-membered ring hydrogen bond, and a 7-membered ring gamma-turn.

  DOI：

  10.1021/ja029514j
• 作为产物：
  描述：

  (R)-2-(2,2-Dimethyl-propionylaminooxy)-4-methyl-pentanoic acid tert-butyl ester 在 1-羟基苯并三唑 、 1-[3-(dimethylamino)-propyl]-3-ethylcarbodiimide methiodide 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 (S)-2-[(R)-2-(2,2-Dimethyl-propionylaminooxy)-4-methyl-pentanoylaminooxy]-3-phenyl-propionic acid tert-butyl ester
  参考文献：
  名称：

  A Reverse Turn Structure Induced by a d,l-α-Aminoxy Acid Dimer

  摘要：

  Our previous work revealed that two adjacent D-a-aminoxy acids could form two homochiral N-O turns, with the backbone folding into an extended helical structure (1.8(8)-helix). Here, we report the conformational studies of linear peptides 3-6, which contain a D,L-alpha-aminoxy acid dimer segment. The NMR and X-ray analysis of 3 showed that it folded into a loop conformation with two heterochiral N-O turns. This loop segment can be used to constrain tetrapeptides 4 and 6 to form a reverse turn structure. H-1 NMR dilution studies, DMSO-d(6) addition studies, and 2D-NOESY data indicated that tetrapeptides 4 and 6 folded into reverse turn conformations featured by a head-to-tail 16-membered-ring intramolecular hydrogen bond. In contrast, tetrapeptide 5 with L-Ala instead of Gly or D-Ala as the N-terminal amino acid could not form the desired reverse turn structure for steric reasons. Quantum mechanics calculations showed that model pentamide 7, with the same substitution pattern of 4, adopted a novel reverse turn conformation featuring two heterochiral N-O turns (each of an 8-membered ring hydrogen bond), a cross-strand 16-membered ring hydrogen bond, and a 7-membered ring gamma-turn.

  DOI：

  10.1021/ja029514j