Nα-Acetyl-Nε-benzyloxycarbonyl-L-lysinamid | 50557-87-4

• 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-Acetyl-Nε-benzyloxycarbonyl-L-lysinamid
• 英文别名: N^α-Acetyl-N^ε-benzyloxycarbonyl-L-lysinamid；Ac-Lys(Z)-NH2
• CAS: 50557-87-4
• 化学式: C₁₆H₂₃N₃O₄
• 分子量: 321.376
• InChiKey: QMCXMQMQJDKLFD-AWEZNQCLSA-N

物化性质

• 熔点：
  162 °C
• 沸点：
  639.4±55.0 °C(Predicted)
• 密度：
  1.174±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.07
• 重原子数：
  23.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  110.52
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Nα-Acetyl-Nε-benzyloxycarbonyl-L-lysinamid 在 palladium on activated charcoal 氢气 作用下， 以 溶剂黄146 为溶剂， 生成 N-α-acetyllysine amide
  参考文献：
  名称：

  [激素-受体相互作用。借助于对碱不稳定的保护基的合成α-促黑素及其信息序列（作者的翻译）]。

  摘要：

  Hormone‐Receptor Interactions. Synthesses of α‐Melanotropin and of Informational Sequences thereof with the Aid of Alcali‐Labile Protecting Groups.The aim of this investigation was to prepare α‐melanotropin and partial sequences thereof for biological investigations in as pure a state as possible. Classical synthesis in solution was chosen as the general approach, because it allows for extensive purification and identification of all intermediates, thus warranting the chemical identity of the products (in contrast to the solidphase methods). The scheme of protection was as follows: for the Nα‐amino groups mostly t‐butoxycarbonyl (BOC‐), sometimes benzyloxycarbonyl (Z‐), for the Nϵ‐amino group of lysine‐(11) 2‐(methylsulfonyl)‐ethoxycarbonyl (MSOC‐), and for the carboxylic acid group of C‐terminal glycine‐(10) 2‐(4‐tolyl‐sulfonyl)‐ethoxy (‐OTSE). This provides for facile and mild selective deprotection of either the α‐amino groups by acidolysis or of the ϵ‐amino group (α‐carboxyl group) by β‐elimination in alcali. A slight molar excess of 0.12N HCl in HCOOH proved to be the method of choice for removing BOC‐; MSOC‐ is stable in acid (even for 30 min in liquid HF) and easily removed in a few minutes by 0.05‐‐0.1N Ba(OH)2; ‐OTSE is removed similarly. Condensation of amino‐acid and peptide derivatives (formation of the peptide link) was performed using active esters (‐ONP; ‐OSU), dicyclohexyl‐carbodiimide (DCCI) with or without 1‐hydroxy‐benzotriazole (HOBT), or carboxylic acid azides wherever histidine was the carboxylic component.More than 50 compounds are described. Those characterized by arabic numerals served to prove that α‐MSH contains two message sequences that are able to trigger melanocyte response: one in the central region ‐His‐Phe‐Arg‐Trp‐, the other in the C‐terminal portion ‐Gly‐Lys‐Pro‐Val · NH2 of the molecule [3].

  DOI：

  10.1002/hlca.19750580724
• 作为产物：
  描述：

  N^ε-(benzyloxycarbonyl)-N^α-(tert-butoxycarbonyl)-L-lysinamide 在 N-乙基吗啉 、 吡啶 、 盐酸 作用下， 以 甲酸 、 N,N-二甲基甲酰胺 为溶剂， 生成 Nα-Acetyl-Nε-benzyloxycarbonyl-L-lysinamid
  参考文献：
  名称：

  [激素-受体相互作用。借助于对碱不稳定的保护基的合成α-促黑素及其信息序列（作者的翻译）]。

  摘要：

  Hormone‐Receptor Interactions. Synthesses of α‐Melanotropin and of Informational Sequences thereof with the Aid of Alcali‐Labile Protecting Groups.The aim of this investigation was to prepare α‐melanotropin and partial sequences thereof for biological investigations in as pure a state as possible. Classical synthesis in solution was chosen as the general approach, because it allows for extensive purification and identification of all intermediates, thus warranting the chemical identity of the products (in contrast to the solidphase methods). The scheme of protection was as follows: for the Nα‐amino groups mostly t‐butoxycarbonyl (BOC‐), sometimes benzyloxycarbonyl (Z‐), for the Nϵ‐amino group of lysine‐(11) 2‐(methylsulfonyl)‐ethoxycarbonyl (MSOC‐), and for the carboxylic acid group of C‐terminal glycine‐(10) 2‐(4‐tolyl‐sulfonyl)‐ethoxy (‐OTSE). This provides for facile and mild selective deprotection of either the α‐amino groups by acidolysis or of the ϵ‐amino group (α‐carboxyl group) by β‐elimination in alcali. A slight molar excess of 0.12N HCl in HCOOH proved to be the method of choice for removing BOC‐; MSOC‐ is stable in acid (even for 30 min in liquid HF) and easily removed in a few minutes by 0.05‐‐0.1N Ba(OH)2; ‐OTSE is removed similarly. Condensation of amino‐acid and peptide derivatives (formation of the peptide link) was performed using active esters (‐ONP; ‐OSU), dicyclohexyl‐carbodiimide (DCCI) with or without 1‐hydroxy‐benzotriazole (HOBT), or carboxylic acid azides wherever histidine was the carboxylic component.More than 50 compounds are described. Those characterized by arabic numerals served to prove that α‐MSH contains two message sequences that are able to trigger melanocyte response: one in the central region ‐His‐Phe‐Arg‐Trp‐, the other in the C‐terminal portion ‐Gly‐Lys‐Pro‐Val · NH2 of the molecule [3].

  DOI：

  10.1002/hlca.19750580724

文献信息

• Partial molar volumes and heat capacities of the N-acetyl amide derivatives of the amino acids asparagine, glutamine, tyrosine, and lysine monohydrochloride in aqueous solution at temperatures from T=288.15K to T=328.15K
  作者：Jin L. Liu、Andrew W. Hakin、Gavin R. Hedwig

  DOI：10.1016/j.jct.2006.03.015

  日期：2006.12

  Abstract The partial molar volumes, V 2 ∘ , and partial molar heat capacities, C p , 2 ∘ , at infinite dilution have been determined for the compounds N -acetylasparaginamide, N -acetylglutaminamide, N -acetyltyrosinamide, and N -acetyllysinamide monohydrochloride in aqueous solution at T = (288.15, 298.15, 313.15, and 328.15) K. These results, along with the literature data for the compound N -acetylglycinamide

  摘要 在无限稀释条件下，测定了化合物 N-乙酰天冬酰胺、N-乙酰谷氨酰胺、N-乙酰酪氨酸酰胺和 N-乙酰赖氨酰胺单盐酸盐水溶液的偏摩尔体积 V 2 ∘ 和偏摩尔热容 C p , 2 ∘ 。 T = (288.15, 298.15, 313.15, 和 328.15) K 时的溶液。这些结果，连同化合物 N-乙酰甘氨酰胺的文献数据，已被用于计算氨基酸侧链对热力学性质的贡献。将这些侧链贡献与使用小肽作为侧链模型化合物获得的贡献进行比较。
• <b>Synthesis of Some N-Lipoyl Amino Acids and Peptides</b>
  作者：Koji. Daigo、William T. Brady、Lester J. Reed

  DOI：10.1021/ja00863a031

  日期：1962.2