Troc-alanine | 67451-46-1

• 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: Troc-alanine
• 英文别名: N-Troc alanine；Troc-L-Ala；(2S)-2-(2,2,2-trichloroethoxycarbonylamino)propanoic acid
• CAS: 67451-46-1
• 化学式: C₆H₈Cl₃NO₄
• 分子量: 264.493
• InChiKey: DKNLSCDOJDESHR-VKHMYHEASA-N

物化性质

• 沸点：
  377.6±42.0 °C(Predicted)
• 密度：
  1.564±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Troc-alanine 在 4-二甲氨基吡啶 、 lithium hydroxide 、 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 calcium carbonate 、 碘甲烷 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 、 叔丁醇 为溶剂， 生成 (4S,5R,6E,8E)-4,6,8,10,10-pentamethyl-3-methylidene-5-[2-[[(2S)-3-methyl-2-[methyl-[(2S)-2-(2,2,2-trichloroethoxycarbonylamino)propanoyl]amino]butanoyl]amino]acetyl]oxyundeca-6,8-dienoic acid
  参考文献：
  名称：

  Synthesis of Epiantillatoxin, a Stereoisomer of the Potent Ichthyotoxin from Lyngbya majuscula

  摘要：

  DOI：

  10.1021/ja983334l
• 作为产物：
  描述：

  L-丙氨酸 、 氯甲酸-2,2,2-三氯乙酯 在 sodium hydroxide 作用下， 以73%的产率得到Troc-alanine
  参考文献：
  名称：

  N-2,2,2-Trichloroethoxycarbonyl-L-amino Acids

  摘要：

  DOI：

  10.1055/s-1981-29408

文献信息

• Synthetic studies towards cyclic peptides. Concise synthesis of thiazoline and thiazole containing amino acids
  作者：Michael North、Gerald Pattenden

  DOI：10.1016/s0040-4020(01)81482-4

  日期：——

  Concise and efficient syntheses of optically pure thiazoline and thiazole containing amino acids of the constitution (26) and (27), based on simple condensation reactions between cysteine esters and N-protected imino ethers (22) and (25) derived from chiral amino acids, are described. The synthetic procedures are compatible with a range of amino acid side chains and protecting groups, and allow the

  基于半胱氨​​酸酯与手性氨基酸衍生的N-保护的亚氨基醚（22）和（25）之间的简单缩合反应，可以高效，高效地合成结构纯净的噻唑啉和噻唑结构氨基酸（26）和（27）进行说明。合成程序可与一系列氨基酸侧链和保护基团兼容，并允许制备各种小的光学纯肽，即（32）和（34），适合于修饰天然存在的环状肽，例如赖索胺（3） ）和（4）。
• A Novel Synthesis of N-But-3-enyl-α- and β-Amino Acids
  作者：Andrew Hughes、T. Van Nguyen、Robert Brownlee

  DOI：10.1055/s-0028-1088072

  日期：2009.6

  N-But-3-enyl-α- and β-amino acids can be prepared by cleaving 1,3-oxazolidin-5-ones and 1,3-oxazinan-6-ones in the presence of allylsilanes and boron trifluoride etherate at room temperature in good to excellent yields. 1,3-oxazolidin-5-ones - 1,3-oxazinan-6-ones - amino acids - allylations - Lewis acids

  可以通过在室温下在烯丙基硅烷和三氟化硼醚化物存在下裂解1,3-恶唑烷五-5-酮和1,3-恶嗪南-6-酮来制备N-丁基-3-烯基-α和β-氨基酸温度高到优异的产量。 1,3-恶唑烷丁-5-酮-1,3-恶嗪南-6酮-氨基酸-烯丙基化-路易斯酸
• Synthesis of functionalised β-keto amides by aminoacylation/domino fragmentation of β-enamino amides
  作者：Pavel Yanev、Plamen Angelov

  DOI：10.3762/bjoc.14.238

  日期：——

  Ethylenediamine-derived β-enamino amides are used as equivalents of amide enolate synthons in C-acylation reactions with N-protected amino acids. Domino fragmentation of the obtained intermediates leads to functionalised β-keto amides, bearing a protected amino group in their side chain.

  乙二胺衍生的β-烯胺酰胺在与N-保护的氨基酸进行C-酰化反应中用作酰胺烯酸酯合成子的等价物。所得中间体的多米诺断裂导致官能化的β-酮酰胺，在其侧链带有受保护的氨基。
• Comparative Lipase-Catalyzed Hydrolysis of Ethylene Glycol Derived Esters. The 2-Methoxyethyl Ester as a Protective Group in Peptide and Glycopeptide Synthesis
  作者：Markus Gewehr、Horst Kunz

  DOI：10.1055/s-1997-1374

  日期：1997.12

  Comparison of the lipase-catalyzed cleavage of polar esters derived from ethylene glycol proved 2-methoxyethyl (ME) esters most favorable protecting groups for the carboxylic function of peptides and glycopeptides. They combine high substrate acceptance and high yields of hydrolysis with favorable physiochemical properties and advantageous solubility. The application of this polar ester as protecting group was extended to N-glycosylated amino acids and N-glycopeptides. The selective removal of ME esters by lipases was achieved under mild conditions (pH 7.0 and 37°C), leaving all other linkages including peptide bonds and other ester protecting groups unaffected.

  乙二醇衍生的极性酯在脂肪酶催化下的水解比较表明，2-甲氧乙基（ME）酯是肽和糖肽的羧基功能基团最有利的保护基。它们结合了高底物接受性和高水解产率，同时具有良好的物理化学特性和优越的溶解性。该极性酯作为保护基的应用扩展到N-糖基化氨基酸和N-糖肽。在温和条件下（pH 7.0和37°C），有效地选择性去除ME酯，而不影响其他连接，包括肽键和其他酯保护基。
• Synthesis and biological evaluation of triazole analogues of antillatoxin
  作者：Ryosuke Goto、Ken Okura、Hayato Sakazaki、Tatsuya Sugawara、Shigeru Matsuoka、Masayuki Inoue

  DOI：10.1016/j.tet.2011.05.012

  日期：2011.9

  Antillatoxin 1, a cyclic lipopeptide, is known as an activator of voltage-gated sodium channels and exhibits potent neurotoxicity toward Neuro 2a mouse neuroblastoma cells. To investigate the biological effects of the side-chain structures at C5 and C5' in detail, we planned SAR studies of C5- and C5'-modified antillatoxin analogues. To diversify the structures at the last step of the synthesis, two key intermediates 4 and 6 possessing terminal alkynes at the C5- and C5'-positions were designed and synthesized using two distinct strategies. Sixteen side-chain derivatives were then prepared from 4 and 6 by coupling with a wide variety of azides via click chemistry, and subjected to the cytotoxicity assay. Although almost all of the C5-substituted analogues exhibited no cytotoxicity, the C5'-substituted analogues showed modest cytotoxicity. These results showed that C5' is more tolerant than C5 to structural modifications. The present SAR study will provide valuable information for designing new antillatoxin-based molecular probes for neuroscience research. (C) 2011 Elsevier Ltd. All rights reserved.