N-tert-butoxycarbonyl-L-leucine p-nitroanilide | 114684-52-5

• 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: N-tert-butoxycarbonyl-L-leucine p-nitroanilide
• 英文别名: Boc-L-Leu-pNA；Boc-Leu-p-NA；Carbamic acid, [3-methyl-1-[[(4-nitrophenyl)amino]carbonyl]butyl]-, 1,1-dimethylethyl ester, (S)-；tert-butyl N-[(2S)-4-methyl-1-(4-nitroanilino)-1-oxopentan-2-yl]carbamate
• CAS: 114684-52-5
• 化学式: C₁₇H₂₅N₃O₅
• 分子量: 351.403
• InChiKey: CBOPJGUETNQXGB-AWEZNQCLSA-N

物化性质

• 熔点：
  123-125 °C
• 沸点：
  542.4±35.0 °C(Predicted)
• 密度：
  1.187±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  113
• 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-leucine p-nitroanilide 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 以78.3 %的产率得到L-亮氨酸-4-硝基苯胺
  参考文献：
  名称：

  CN115974752

  摘要：

  公开号：
• 作为产物：
  描述：

  异氰酸对硝基苯 生成 N-tert-butoxycarbonyl-L-leucine p-nitroanilide
  参考文献：
  名称：

  SHIOIRI, TAKAYUKI;MURATA, MITSUO;HAMADA, YASUMASA, CHEM. AND PHARM. BULL., 35,(1987) N 7, 2698-2704

  摘要：

  DOI：

文献信息

• New methods and reagents in organic synthesis. 69. A new synthesis of .ALPHA.-amino acid and peptide amides of aromatic amines using a modified Curtius reaction with diphenyl phosphorazidate.
  作者：TAKAYUKI SHIOIRI、MITSUO MURATA、YASUMASA HAMADA

  DOI：10.1248/cpb.35.2698

  日期：——

  As a basic study on the efficient synthesis of chromogenic and fluorogenic peptidase substrates, we investigated possible general methods for the synthesis of α-amino acid and peptide amides of aromatic amines. Preparation of Boc-L-Leu-pNA (1) as a model compound was attempted by (1) the coupling of Boc-L-Leu-OH with p-nitroaniline, (2) the reaction of Boc-L-Leu OH with p-nitrophenyl isocyanate, and (3) the reaction of Boc-L-Leu-OH with the product formed from p-nitrobenzoic acid through the modified Curtius reaction with diphenyl phosphorazidate ((C6H5O) 2P (O) N3) in a one-pot process. The third method was found to be a general and efficient method for the preparation of α-amino acid amides of aromatic amines. Application of this method to the preparation of a peptidase substrate, Bz-L-Ile-L-Glu (OMe) -Gly-L-Arg-pNA (2), has also been successfully achieved.

  作为染料和荧光素酶底物高效合成的基础研究，我们探索了合成芳香胺类α-氨基酸和肽酰胺的可能通用方法。通过以下三种方法尝试制备模型化合物Boc-L-Leu-pNA (1)：(1) Boc-L-Leu-OH与对硝基苯胺的偶联反应，(2) Boc-L-Leu-OH与对硝基苯基异氰酸酯的反应，以及(3) 在一步法中将Boc-L-Leu-OH与通过二苯基磷酰叠氮((C6H5O) 2P (O) N3)改进的Curtius反应生成的对硝基苯甲酸产物反应。发现第三种方法是制备芳香胺类α-氨基酸酰胺的一种通用且高效的方法。这种方法也已成功应用于制备肽酶底物Bz-L-Ile-L-Glu (OMe) -Gly-L-Arg-pNA (2)。
• Reinvestigation of the Phosphazo Method and Synthesis of<i>N</i>-(<i>t</i>-Butoxycarbonyl)-L-arginine<i>p</i>-Nitroanilide and a Chromogenic Enzyme Substrate for the Factor Xa
  作者：Hidekazu Oyamada、Takashi Saito、Shinsaku Inaba、Masaaki Ueki

  DOI：10.1246/bcsj.64.1422

  日期：1991.4

  Reaction conditions for the phosphazo method were reinvestigated in order to apply this method to the synthesis of p-nitroanilide(pNA)s of t-butoxycarbonyl(Boc)-and benzyloxycarbonyl(Z)-amino acids.

  为将磷氮法应用于合成对硝基苯胺(pNA)的叔丁氧羰基(Boc)和苄氧羰基(Z)氨基酸，重新研究了反应条件。
• Kinetically controlled peptide bond formation in anhydrous alcohol catalyzed by the industrial protease alcalase
  作者：Shui Tein Chen、Shiah Yun Chen、Kung Tsung Wang

  DOI：10.1021/jo00051a052

  日期：1992.12

  The industrial alkaline protease alcalase has been found to be very stable (half life > 5 days in ethanol or 2-methyl-2-propanol) and active in alcoholic solvents (except methanol). Procedures have been developed for alcalase-catalyzed, kinetically controlled peptide bond formation in anhydrous alcohol(ethanol, 2-methyl-2-propanol). Studies of the selectivity of an alcalase-catalyzed reaction show that only L-amino acid acyl donors are substrates at the p-1 subsite of alcalase; at the p-1' subsite both D- and L-amino acid nucleophiles are substrates. Other amino compounds such as benzylamine and phenylhydrazine are good nucleophiles. Studies of the effect of the water content of the reaction solution on the yield in the synthesis of Moz-Phe-Leu-NH2 showed that the 95% yield obtained in anhydrous 2-methyl-2-propanol was decreased to 48% in 2-methyl-2-propanol containing 4.86% water.
• OYAMADA, HIDEKAZU;SAITO, TAKASHI;INABA, SHINSAKU;UEKI, MASAAKI, BULL. CHEM. SOC. JAP., 64,(1991) N, C. 1422-1424
  作者：OYAMADA, HIDEKAZU、SAITO, TAKASHI、INABA, SHINSAKU、UEKI, MASAAKI

  DOI：——

  日期：——
• SHIOIRI, TAKAYUKI;MURATA, MITSUO;HAMADA, YASUMASA, CHEM. AND PHARM. BULL., 35,(1987) N 7, 2698-2704
  作者：SHIOIRI, TAKAYUKI、MURATA, MITSUO、HAMADA, YASUMASA

  DOI：——

  日期：——