benzyl N-(N-(tert-butyloxycarbonyl)phenylalanyl)-L-aziridine-2-carboxylate | 131353-64-5

• 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: benzyl N-(N-(tert-butyloxycarbonyl)phenylalanyl)-L-aziridine-2-carboxylate
• 英文别名: benzyl N-[N-(tert-butyloxycarbonyl)phenylalanyl]-L-aziridine-2-carboxylate；benzyl (2S)-1-[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]aziridine-2-carboxylate
• CAS: 131353-64-5
• 化学式: C₂₄H₂₈N₂O₅
• 分子量: 424.497
• InChiKey: ZQSWNNKWFLABJZ-JRPFNRNASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.08
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  84.71
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  BOC-L-苯丙氨酸 、 (S)-2-氮丙啶甲酸 苄基 酯 在 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以52%的产率得到benzyl N-(N-(tert-butyloxycarbonyl)phenylalanyl)-L-aziridine-2-carboxylate
  参考文献：
  名称：

  Active-site-directed modification of subtilisin

  摘要：

  This paper describes the development of several competitive inhibitors and mechanism-based inactivators of subtilisin BPN'. Various methyl arylalkanesulfonates were prepared and shown to be either competitive inhibitors or selective methylating reagents for the epsilon-2-N of the active-site His. Styrene sulfonyl chloride was shown to be a good covalent inactivator and benzyl N-(N-Boc-L-phenylalanyl)-L-aziridine-2-carboxylate was a strong competitive inhibitor. The second-order rate constant of inactivation and the K(i) of the enzyme reacting with the methylating reagents and other inactivators were determined. The methylated enzyme was purified to homogeneity and the kinetic constants for the enzyme-catalyzed ester and amide hydrolyses were determined. It was established that the methylated enzyme lost most of the amidase activity while the esterase activity was still significant and useful for peptide synthesis via aminolysis. A mechanism involving ring flipping of the active-site imidazole, first proposed for methylchymotrypsin activity, was also proposed to explain methylsubtilisin-catalyzed reactions.

  DOI：

  10.1021/ja00006a052

文献信息

• ZHONG, ZIYANG;BIBBS, JEFFREY A.;YUAN, WEI;WONG, CHI-HUEY, J. AMER. CHEM. SOC., 113,(1991) N, C. 2259-2262
  作者：ZHONG, ZIYANG、BIBBS, JEFFREY A.、YUAN, WEI、WONG, CHI-HUEY

  DOI：——

  日期：——