L-leucine tert-butylamide hydrochloride | 151240-05-0

• 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: L-leucine tert-butylamide hydrochloride
• 英文别名: H-Leu-NH(t-Bu)
• CAS: 151240-05-0
• 化学式: C₁₀H₂₂N₂O*ClH
• 分子量: 222.758
• InChiKey: LXXBAINFTBVJKY-QRPNPIFTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  55.12
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  L-leucine tert-butylamide hydrochloride 在 palladium on activated charcoal N-甲基吗啉 、 sodium azide 、 氢气 、 氯化铵 、 间氯过氧苯甲酸 、 氯甲酸异丁酯 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， -15.0~25.0 ℃ 、206.84 kPa 条件下， 反应 66.5h， 生成 N-<amino-2-hydroxy-1-cyclopentyl>acetyl> leucine t-butylamide
  参考文献：
  名称：

  Progress towards new conformationally constrained HIV-1 protease inhibitors

  摘要：

  Two series of molecules containing a trisubstituted cyclopentyl group as the central unit were synthesized and evaluated as inhibitors of HIV-1 protease (HIV PR). In the first series of molecules (13-20), the central unit A, 3-(N-acyl)amino-2-hydroxy-1-cyclopentylacetyl, was designed so as to reproduce three of the central interactions found in the 'classical' complex HIV PR-JG365 inhibitor. Significant inhibitions (IC50 similar to 10 mu M) were obtained with compound 20 in which the central unit was elongated by Z-Ile-Phe at the N-terminus and by Val-OMe at the C-terminus. In the second series of molecules (21-28), the central unit B, 3-hydroxy-2-(N-acyl)amino-1-cyclopentylacetyl, was obtained in the first steps of the synthesis. Unexpectedly better inhibitions were observed with these derivatives (K-i = 2 mu M for compound 28). Docking and molecular dynamics simulations performed with compound 28 into HIV PR suggested that the HIV PR-28 complex should have a structure analogous to that of the recently described HIV PR-urea complex.

  DOI：

  10.1016/0223-5234(96)88308-5

文献信息

• Dehydrooligopeptides. XV. Useful Syntheses of Dehydrodipeptides by the Enzymatic Coupling of<i>α</i>-Dehydroglutamate with Various<i>α</i>-Amino Acid Amides Using Proteases
  作者：Chung-gi Shin、Masashi Seki、Takeshi Kakusho、Nobuyuki Takahashi

  DOI：10.1246/bcsj.66.2048

  日期：1993.7

  of α-ester of 1 with H–AA–NHR took place to give Cbz–ΔGlu(OMe)–AA–NHR, while in the case of CT the coupling of γ-ester of 1 proceeded predominantly to give Cbz–ΔGlu(AA–NHR)–OMe. The present study suggests that both papain and CT may become a versatile tool for the organic synthesis by the coupling of not only ΔGlu derivatives but also the other α-dehydroamino acids with α-amino acids or peptides.

  通过 α,γ-二甲基 N-苄氧羰基 (Z)-α-脱氢谷氨酸酯 [Cbz-ΔGlu(OMe)-OMe] 偶联合成各种脱氢二肽的新型酶法；图 1] 描述了使用蛋白酶（如木瓜蛋白酶和 α-胰凝乳蛋白酶 A（CT））与 α-氨基酸酰胺（H-AA-NHR）。发现木瓜蛋白酶和 CT 对 1 的催化作用存在显着差异。在木瓜蛋白酶的情况下，1 的 α-酯与 H-AA-NHR 发生选择性偶联，得到 Cbz-ΔGlu(OMe) –AA–NHR，而在 CT 的情况下，1 的 γ-酯的偶联主要产生 Cbz–ΔGlu(AA–NHR)–OMe。目前的研究表明，木瓜蛋白酶和 CT 可能成为有机合成的通用工具，不仅可以通过 ΔGlu 衍生物而且还可以将其他 α-脱氢氨基酸与 α-氨基酸或肽偶联。
• Extended scope of enantiomer resolution with chiral diamide phases in liquid chromatography
  作者：Akira. Dobashi、Yasuo. Dobashi、Kyo. Kinoshita、Shoji. Hara

  DOI：10.1021/ac00169a032

  日期：1988.9.15