Cbz-L-Gln-NH₂ | 76491-40-2

• 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-L-Gln-NH₂
• 英文别名: Cbz-Gln-NH2；N-benzyloxycarbonyl-L-glutamic acid diamide；N-Benzyloxycarbonyl-L-glutaminsaeure-diamid；(S)-Benzyl N-(1,5-diamino-1,5-dioxopentan-2-yl)carbamate；benzyl N-[(2S)-1,5-diamino-1,5-dioxopentan-2-yl]carbamate
• CAS: 76491-40-2；92043-67-9；2650-66-0
• 化学式: C₁₃H₁₇N₃O₄
• 分子量: 279.296
• InChiKey: GTEQUDFRRSOJGP-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  125
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Cbz-L-Gln-NH₂ 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成 L-glutamic acid diamide
  参考文献：
  名称：

  Synthesis and Activity of Dipeptides, Linked to Targeting Ligands, as Specific NK Cell Enhancers

  摘要：

  Water soluble analogues of the lipophilic immunostimulant, octadecyl D-alanyl-L-glutamine, BCH-527, were synthesized and evaluated for the ability to stimulate natural killer (NK) cells. One of these compounds in which the octadecyl chain of BCH-527 was replaced with a shorter chain alcohol, 6-(D-alanyl-L-glutaminylamino)hexan-1-ol, 9, displayed an in vitro stimulation of NK cells comparable to that of interleukin 2 (IL 2). However, when the hydroxyl of 9 was linked to L-fucose to yield 1-beta-[6-(D-alanyl-L-glutaminylamino)hex-1-yl]-L-fucopyranose (BCH-2537 1), the observed stimulation of NK cells was greater than that observed with IL 2. Further evaluation of these compounds revealed that the improved in vitro activity of BCH-2537 was more pronounced in vivo. That is, while both compounds significantly increased splenic NK cells, only BCH-2537 significantly increased the activity of these cells in vivo. In terms of a structure-activity relationship, NK cell activity was sensitive to minor structural modifications. It was influenced by conservative substitutions within the dipeptide, the length of the hydrocarbon chain, and the functionality at the end of the chain. No other compound enhanced NK cell activity to the extent exhibited by BCH-2537, although a few were equipotent to 9.

  DOI：

  10.1021/jm970734v
• 作为产物：
  描述：

  Carbobenzoxy-L-glutaminsaeure-1-thioethylester 在 ammonium hydroxide 作用下， 生成 Cbz-L-Gln-NH₂
  参考文献：
  名称：

  Klieger,E.; Gibian,H., Justus Liebigs Annalen der Chemie, 1962, vol. 651, p. 194 - 205

  摘要：

  DOI：

文献信息

• Convenient Preparation of Primary Amides via Activation of Carboxylic Acids with Ethyl Chloroformate and Triethylamine under Mild Conditions
  作者：Takuya Noguchi、Masahiro Sekine、Yuki Yokoo、Seunghee Jung、Nobuyuki Imai

  DOI：10.1246/cl.130096

  日期：2013.6.5

  Primary amides were easily prepared in 22–99% yields from the corresponding carboxylic acids 1 or 5 with NH4Cl via activation with ClCO2Et and Et3N. The enantiomers of the corresponding primary ami...

  通过用 ClCO2Et 和 Et3N 活化，用 NH4Cl 从相应的羧酸 1 或 5 中很容易以 22-99% 的产率制备伯酰胺。相应伯胺的对映体...
• “BOP” as a reagent for mild and efficient preparation of esters
  作者：Moon H. Kim、Dinesh V. Patel

  DOI：10.1016/s0040-4039(00)77257-1

  日期：1994.8

  A simple procedure for preparation of esters under mild conditions employing the BOP reagent is reported. Acid and base labile protecting groups commonly used with amino acids e.g. t-butyl, Fmoc etc., are well tolerated under these conditions. The mechanism and scope of this reaction are briefly discussed.

  报道了一种使用BOP试剂在温和条件下制备酯的简单方法。在这些条件下，对氨基酸通常使用的酸和碱不稳定的保护基（例如叔丁基，Fmoc等）具有很好的耐受性。简要讨论了该反应的机理和范围。
• Enzymatic C-terminal amidation of amino acids and peptides
  作者：Timo Nuijens、Elena Piva、John A.W. Kruijtzer、Dirk T.S. Rijkers、Rob M.J. Liskamp、Peter J.L.M. Quaedflieg

  DOI：10.1016/j.tetlet.2012.05.039

  日期：2012.7

  enzymatic approaches for the conversion of semi-protected amino acid and peptidyl C-terminal α-carboxylic acids into their corresponding amides. In the first approach, the lipase Candida antarctica lipase-B (Cal-B), and in the second approach, the protease Subtilisin A, are used, respectively. We found that by using the ammonium salt of the α-carboxylic acid instead of separate ammonia sources, the enzymatic

  在本文中，我们描述了两种通用且高产的酶促方法，可将半保护的氨基酸和肽基C末端α-羧酸转化为它们相应的酰胺。在第一种方法中，分别使用脂肪酶南极假丝酵母脂肪酶-B（Cal-B），在第二种方法中，分别使用蛋白酶枯草杆菌蛋白酶A。我们发现，通过使用α-羧酸的铵盐代替单独的氨源，酶促酰胺化反应的进行速度大大加快，而没有副反应，并且使产物收率接近定量。
• Peptides and process for their preparation
  申请人：ORTHO PHARMACEUTICAL CORPORATION

  公开号：EP0018793A2

  公开（公告）日：1980-11-12

  A method for solution synthesis of H-SAR-LYS-SAR-GLN-NH2 in good yield and compositions useful therein are disdosed.

  本发明公开了一种以良好收率溶液合成 H-SAR-LYS-SAR-GLN-NH2 的方法及其有用成分。
• Amidation of carboxylic acids via the mixed carbonic carboxylic anhydrides and its application to synthesis of antidepressant (1 S ,2 R )-tranylcypromine
  作者：Tetsuya Ezawa、Yuya Kawashima、Takuya Noguchi、Seunghee Jung、Nobuyuki Imai

  DOI：10.1016/j.tetasy.2017.10.015

  日期：2017.12

  Primary amidations of carboxylic acids 1 or 3 with NH4Cl in the presence of ClCO2Et and Et3N were developed to afford the corresponding primary amides in 22% to quantitative yields. Additionally, we have applied the amidation to the preparation of various amides containing hydroxamic acids and achieved the synthesis of (1S,2R)-tranylcypromine as an antidepressant medicine via Lossen rearrangement. (C) 2017 Elsevier Ltd. All rights reserved.