Cbz-Tyr(Bn)-NH2 | 223593-07-5

• 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: Cbz-Tyr(Bn)-NH2
• 英文别名: Carbamic acid, [(1S)-2-amino-2-oxo-1-[[4-(phenylmethoxy)phenyl]methyl]ethyl]-, phenylmethyl ester；benzyl N-[(2S)-1-amino-1-oxo-3-(4-phenylmethoxyphenyl)propan-2-yl]carbamate
• CAS: 223593-07-5
• 化学式: C₂₄H₂₄N₂O₄
• 分子量: 404.466
• InChiKey: DXXDWMAKDZZZHV-QFIPXVFZSA-N

物化性质

• 熔点：
  183-184 °C
• 沸点：
  656.5±55.0 °C(Predicted)
• 密度：
  1.223±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  90.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  O-苯基-N-叔丁基羰基-L-酪氨酸 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 氯化铵 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以95%的产率得到Cbz-Tyr(Bn)-NH2
  参考文献：
  名称：

  制备伯酰胺的一种选择性方法：Fmoc-1-4-羧酰胺基苯丙氨酸和其他化合物的合成

  摘要：

  开发了一种新的合成伯酰胺的方法，其中在肽合成偶联剂和碱存在下，在室温下用氯化铵处理羧酸。这些温和的条件使羧基能够在具有敏感官能团（例如酯和对碱不稳定的Fmoc保护基）的底物上转化为伯酰胺。

  DOI：

  10.1016/s0040-4039(99)00245-2

文献信息

• A selective method for the preparation of primary amides: Synthesis of Fmoc-l-4-carboxamidophenylalanine and other compounds
  作者：Wei Wang、John S. McMurray

  DOI：10.1016/s0040-4039(99)00245-2

  日期：1999.3

  A new method for the synthesis of primary amides was developed in which carboxylic acids were treated with ammonium chloride in the presence of peptide synthesis coupling agents and base at room temperature. These mild conditions allow the conversion of carboxyl groups to primary amides on substrates possessing sensitive functional groups such as esters and the base-labile Fmoc protecting group.

  开发了一种新的合成伯酰胺的方法，其中在肽合成偶联剂和碱存在下，在室温下用氯化铵处理羧酸。这些温和的条件使羧基能够在具有敏感官能团（例如酯和对碱不稳定的Fmoc保护基）的底物上转化为伯酰胺。
• Synthesis and stereochemical preference of peptide 4-aminocyclophosphamide conjugates as potential prodrugs of phosphoramide mustard for activation by prostate-specific antigen (PSA)
  作者：Yongying Jiang、Robert S. DiPaola、Longqin Hu

  DOI：10.1016/j.bmcl.2009.03.009

  日期：2009.5

  In an effort to develop proteolytically activated prodrugs of phosphoramide mustard by prostate-specific antigen (PSA), a series of tetrapeptide (Cbz-Ser-Ser-Phe-Tyr)-conjugated 4-aminocyclophosphamide (4-NH2-CPA) isomers were synthesized and evaluated as substrates of PSA. The cleavage of the conjugates by PSA were found to be stereoselective as only the two isomers with 4R-configuration were efficiently

  为了开发通过前列腺特异性抗原（PSA）进行蛋白水解活化的磷酰胺芥末的前药，开发了一系列四肽（Cbz-Ser-Ser-Phe-Tyr）共轭的4-氨基环磷酰胺（4-NH 2 -CPA）异构体。合成并评估为PSA的底物。通过PSA偶联物的切割被认为是立体选择性的，因为只有这两种异构体用4 - [R构型被有效地被PSA切割。顺式-（2R，4R）-异构体是PSA的最佳底物，半衰期为12分钟。LC-MS分析该异构体与PSA的孵育溶液表明4-NH 2-CPA在蛋白水解时释放，并迅速降解为具有细胞毒性的磷酰胺芥末。这些结果阐明了PSA对4-NH 2 -CPA肽缀合物的立体化学要求，并证明了这些缀合物作为靶向前列腺癌的潜在PSA活化前药的潜力。
• Efficient synthesis of primary amides using 2-mercaptopyridone-1-oxide-based uronium salts
  作者：Miguel A. Bailén、Rafael Chinchilla、David J. Dodsworth、Carmen Nájera

  DOI：10.1016/s0040-4039(00)01775-5

  日期：2000.12

  S-(1-Oxido-2-pyridinyl)-1,1,3,3-tetramethylthiouronium tetrafluoroborate (TOTT) and hexafluorophosphate (HOTT) are cheap and convenient reagents for the rapid and high-yielding preparation of primary amides when reacted with carboxylic acids and ammonium chloride in the presence of diisopropylethylamine. The reaction is chemoselective and undesired ammonolysis of other sensitive functional groups is not observed. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Ammonium salts from polymer-bound N-hydroxysuccinimide as solid-supported reagents for EDC-mediated amidations
  作者：Rafael Chinchilla、David J Dodsworth、Carmen Nájera、José M Soriano

  DOI：10.1016/s0040-4039(02)02592-3

  日期：2003.1

  New ammonium and alkylammonium salts derived from a polymeric N-hydroxysuccinimide (P-HOSu) have been prepared and used for the amidation of carboxylic acids and amino acids mediated by 1-ethyl-3-(3'-dimethylamino-propyl)carbodiimide hydrochloride (EDC). These polymer-supported ammonium salts afforded the corresponding amides in good yield, without detectable alpha-racemization and with easy recovery of the P-HOSu after the amidation reaction, being especially suitable for the amidation of Fmoc-protected amino acids. (C) 2002 Published by Elsevier Science Ltd.