Nα-benzyloxycarbonyl-arginine methyl ester hydrochloride | 5134-44-1

• 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: Nα-benzyloxycarbonyl-arginine methyl ester hydrochloride
• 英文别名: Cbz-Arg-OMe*HCl；Z-Arg-OMe hydrochloride；methyl (2S)-5-(diaminomethylideneamino)-2-(phenylmethoxycarbonylamino)pentanoate;hydrochloride
• CAS: 5134-44-1
• 化学式: C₁₅H₂₂N₄O₄*ClH
• 分子量: 358.825
• InChiKey: WXXWZTQWEYPQNF-YDALLXLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.93
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  129
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Nα-benzyloxycarbonyl-arginine methyl ester hydrochloride 、 苯胺 在 1,4-dithio-D,L-threitol 、 Carica papaya serine protease papain 作用下， 以82%的产率得到Cbz-Arg-anilide
  参考文献：
  名称：

  Enzymatic Synthesis of C-Terminal Arylamides of Amino Acids and Peptides

  摘要：

  A mild and cost-efficient chemo-enzymatic method for the synthesis of C-terminal arylamides of amino acid and peptides is described. Using the industrial serine protease Alcalase under near-anhydrous conditions, C-terminal arylamides of N-Cbz-protected amino acids and peptides could be obtained from the corresponding C-terminal carboxylic acids, methyl (Me) or benzyl (Bn) esters, in hi-h chemical and enantio- and diastereomeric purities. Yields ranged between 50% and 95% depending on the size of the aryl substituents and the presence of electron-withdrawing substituents. Complete (alpha-C-terminal selectivity could be obtained even in the presence of various unprotected side-chain functionalities such as beta/gamma-carboxyl, hydroxyl, and guanidino groups. In addition, the use of the cysteine protease papain and the lipase Cal-B gave anilides in high yields. The chemo-enzymatic synthesis of arylamides proved to be completely free of racemization, in contrast to the state-of-the-art chemical methods.

  DOI：

  10.1021/jo900634g
• 作为产物：
  描述：

  甲醇 、 Cbz-L-精氨酸盐酸盐 在 氯化亚砜 作用下， 以100%的产率得到Nα-benzyloxycarbonyl-arginine methyl ester hydrochloride
  参考文献：
  名称：

  Enzymatic Synthesis of C-Terminal Arylamides of Amino Acids and Peptides

  摘要：

  A mild and cost-efficient chemo-enzymatic method for the synthesis of C-terminal arylamides of amino acid and peptides is described. Using the industrial serine protease Alcalase under near-anhydrous conditions, C-terminal arylamides of N-Cbz-protected amino acids and peptides could be obtained from the corresponding C-terminal carboxylic acids, methyl (Me) or benzyl (Bn) esters, in hi-h chemical and enantio- and diastereomeric purities. Yields ranged between 50% and 95% depending on the size of the aryl substituents and the presence of electron-withdrawing substituents. Complete (alpha-C-terminal selectivity could be obtained even in the presence of various unprotected side-chain functionalities such as beta/gamma-carboxyl, hydroxyl, and guanidino groups. In addition, the use of the cysteine protease papain and the lipase Cal-B gave anilides in high yields. The chemo-enzymatic synthesis of arylamides proved to be completely free of racemization, in contrast to the state-of-the-art chemical methods.

  DOI：

  10.1021/jo900634g

文献信息

• Neue Oligopeptidylargininolderivate und deren Homologe, Verfahren zu deren Herstellung, deren Verwendung und diese enthaltende Mittel
  申请人：BEHRINGWERKE Aktiengesellschaft

  公开号：EP0192135A2

  公开（公告）日：1986-08-27

  @ Die Erfindung betrifft neue Peptidylargininolderivate und deren Homologe mit der allgemeinen Formel wobei X ein Wasserstoffatom oder eine in der Peptidchemie übliche, bekannte Schutzgruppe ist, D-Phe D-Phenylalanin ist, Pro L-Prolin ist, A ein ω-Guanidino-β-aminoalkanolrest der Formel -NHCH[(CH2)mNHC(NH)NH2]CH2O- mit m = 2 bis 5 C-Atomen, vorzugsweise ein Argininolrest oder ein Homoargininolrest ist, Y ein Wasserstoffatom oder eine Ester-bildende Gruppe ist, B ein Säurerest ist n 0, 1 oder 2 ist, Verfahren zur Herstellung dieser Verbindungen, pharmazeutische Mittel, die diese Mittel enthalten sowie die Verwendung dieser Mittel als Thrombininhibitoren.

  @ 本发明涉及通式如下的新型肽精醇衍生物及其同系物 式中 X 是氢原子或肽化学中常用的已知保护基团、 D-Phe 是 D-苯丙氨酸、 Pro 是 L-脯氨酸、 A 是式-NHCH[(CH2)mNHC(NH)NH2]CH2O-的ω-胍基-β-氨基烷醇基，m = 2 至 5 个 C 原子、 最好是精氨醇基或均精氨醇基、 Y 是氢原子或形成酯的基团、 B 是酸残基 n 为 0、1 或 2、 这些化合物的制备工艺、含有这些化合物的药物组合物以及这些化合物作为凝血酶抑制剂的用途。
• Almeidaa, Joao A. S.; Morana, Maria C.; Infanteb, Maria R., ARKIVOC, 2010, vol. 2010, # 5, p. 34 - 50
  作者：Almeidaa, Joao A. S.、Morana, Maria C.、Infanteb, Maria R.、Paisa, Alberto A. C. C.

  DOI：——

  日期：——
• Enzymatic Synthesis of <i>C</i>-Terminal Arylamides of Amino Acids and Peptides
  作者：Timo Nuijens、Claudia Cusan、John A. W. Kruijtzer、Dirk T. S. Rijkers、Rob M. J. Liskamp、Peter J. L. M. Quaedflieg

  DOI：10.1021/jo900634g

  日期：2009.8.7

  A mild and cost-efficient chemo-enzymatic method for the synthesis of C-terminal arylamides of amino acid and peptides is described. Using the industrial serine protease Alcalase under near-anhydrous conditions, C-terminal arylamides of N-Cbz-protected amino acids and peptides could be obtained from the corresponding C-terminal carboxylic acids, methyl (Me) or benzyl (Bn) esters, in hi-h chemical and enantio- and diastereomeric purities. Yields ranged between 50% and 95% depending on the size of the aryl substituents and the presence of electron-withdrawing substituents. Complete (alpha-C-terminal selectivity could be obtained even in the presence of various unprotected side-chain functionalities such as beta/gamma-carboxyl, hydroxyl, and guanidino groups. In addition, the use of the cysteine protease papain and the lipase Cal-B gave anilides in high yields. The chemo-enzymatic synthesis of arylamides proved to be completely free of racemization, in contrast to the state-of-the-art chemical methods.