Cbz-Phe-D-Phe-NH2

• 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-Phe-D-Phe-NH2
• 英文别名: N-cbz-L-Phe-D-Phe-NH2；benzyl N-[(2S)-1-[[(2R)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]carbamate
• 化学式: C₂₆H₂₇N₃O₄
• 分子量: 445.518
• InChiKey: XWEGJTXMZBKDSX-PKTZIBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  111
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  Cbz-L-Phe-D-Phe-OH 在 氯化铵 、 三乙胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.17h， 生成 Cbz-Phe-D-Phe-NH2
  参考文献：
  名称：

  各种含二肽药物类似物的绿色非对映特异性合成及贝克酵母的药物释放

  摘要：

  我们已经成功地以 76–99% 的收率和 70–>99% 的去氧化酶绿色和经济地合成了各种二肽和含二肽的药物类似物，在 -15 °C 的水性 THF 中以 79–97% 的去氧化酶的收率在 -15 °C 下通过通过相应羧酸的活化得到混合碳酸酐。我们观察到苯胺l -Phe- l -Phe-NHC 6 H 4 -4-OH 是一种脱保护药物类似物，在饥饿条件下被贝克酵母在l-苯丙氨酸 ( l -Phe) 的C端裂解条件，然后处理新鲜制备的 PhCH 2 CH 2 CO 2 CO 2Et 从 3-苯基丙酸、ClCO 2 Et 和 Et 3 N 在 MeCN 中得到 PhCH 2 CH 2 CONHC 6 H 4 -4-OH 和 PhCH 2 CH 2 CO - 1 -Phe-NHC 6 H 4 -4-OH收益率分别为 46% 和 42%。有趣的是，贝克酵母对l -Phe- d -Phe-NHC 6

  DOI：

  10.1016/j.tet.2022.133102

文献信息

• Convenient primary amidation of N-protected phenylglycine and dipeptides without racemization or epimerization
  作者：Takuya Noguchi、Seunghee Jung、Nobuyuki Imai

  DOI：10.1016/j.tetlet.2013.11.042

  日期：2014.1

  Primary amidation of N-protected phenylglycine and dipeptide proceeded easily to afford the corresponding amides in 57–95% yields with 99% ee and 81–99% de, respectively. The procedure is very easy to avoid racemization and epimerization of the products in the reactions by keeping exactly the reaction temperature at −15 °C when the activation of carboxylic acids, followed by the reaction of the mixed

  N-保护的苯基甘氨酸和二肽的初次酰胺化反应容易进行，以57-95％的收率分别提供了99％ee和81-99％de的相应酰胺。通过在羧酸活化时将反应温度精确地保持在-15°C，然后使混合的碳羧酸酐与NH 4 Cl反应，该过程很容易避免反应中产物的外消旋和差向异构化。
• α-Chymotrypsin-catalyzed peptide synthesis in frozen aqueous solution using N-protected amino acid carbamoylmethyl esters as acyl donors
  作者：Sayed Mohiuddin Abdus Salam、Ken-ichi Kagawa、Katsuhiro Kawashiro

  DOI：10.1016/j.tetasy.2005.10.042

  日期：2006.1

  A kinetically controlled peptide synthesis catalyzed by alpha-chymotrypsin was performed in frozen aqueous solution (ice, -24 degrees C). The yield of the peptide was significantly improved by the use of the carbamoylmethyl (Cam) ester as the acyl donor instead of the conventional ethyl ester. The peptide yield increased up to ca. 90% when N-benzyloxycarbonyl (CBZ)-Phe-OCam and H-Phe-NH2 were used as the acyl donor and nucleophile, respectively. Such an improvement of the peptide yield in ice was also observed in the coupling of other CBZ-amino acid Cam esters as acyl donors. Furthermore, this approach was applied to the synthesis of peptides containing D-amino acids. The peptides such as CBZ-D-Phe-Phe-NH2, CBZ-Phe-D-Phe-NH2 and CBZ-D-Phe-D-Phe-NH2 were also obtained in excellent to moderate yields in ice. A high diastereoselectivity towards the L-L peptide was observed when the racemic amino acid Cam ester was used as the acyl donor in ice. (c) 2005 Elsevier Ltd. All rights reserved.
• Cross-Linked Crystals of Subtilisin:  Versatile Catalyst for Organic Synthesis
  作者：Yi-Fong Wang、Kirill Yakovlevsky、Bailing Zhang、Alexey L. Margolin

  DOI：10.1021/jo9618334

  日期：1997.5.1

  Cross-linked enzyme crystals (CLECs) of subtilisin exhibit excellent activity in aqueous and various organic solvents. This catalyst is more stable than the native enzyme in both aqueous and mixed aqueous/organic solutions. Subtilisin-CLEC was shown to be a versatile catalyst. It was used for the syntheses of peptides and peptidomimetics, mild hydrolysis of amino acid and peptide amides, enantio- and regioselective reactions, and transesterifications.