N2-(叔丁氧羰基)-N6-[[2-(甲基磺酰基)乙氧基]羰基]-L-赖氨酸4-硝基苯基酯 | 58082-65-8

• 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
• 中文名称: N2-(叔丁氧羰基)-N6-[[2-(甲基磺酰基)乙氧基]羰基]-L-赖氨酸4-硝基苯基酯
• 英文名称: BOC-Lys(MSC)-ONP
• 英文别名: p-Nitrophenyl N2-(tert-butoxycarbonyl)-N6-((2-(methylsulphonyl)ethoxy)carbonyl)-L-lysinate；(4-nitrophenyl) (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-6-(2-methylsulfonylethoxycarbonylamino)hexanoate
• CAS: 58082-65-8
• 化学式: C₂₁H₃₁N₃O₁₀S
• 分子量: 517.557
• InChiKey: AMMIWIHTJFNQDK-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  35
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  191
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  N2-(叔丁氧羰基)-N6-[[2-(甲基磺酰基)乙氧基]羰基]-L-赖氨酸4-硝基苯基酯 、 三氟乙酸 生成 H-Lys(MSC)-ONP trifluoroacetate
  参考文献：
  名称：

  Diaz; Cazaubon; Demarne, European Journal of Medicinal Chemistry, 1985, vol. 20, # 3, p. 219 - 227

  摘要：

  DOI：
• 作为产物：
  描述：

  对硝基苯酚 、 N2-[(1,1-二甲基乙氧基)羰基]-N6-[[2-(甲基磺酰基)乙氧基]羰基]-L-赖氨酸 在 吡啶 、 N,N'-二环己基碳二亚胺 作用下， 生成 N2-(叔丁氧羰基)-N6-[[2-(甲基磺酰基)乙氧基]羰基]-L-赖氨酸4-硝基苯基酯
  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

• Hormon-Rezeptor-Wechselwirkungen. Synthese von α-Melanotropin und von informationstragenden Teilsequenzen unter Verwendung alkalilabiler Schutzgruppen
  作者：Alex Eberle、Jean-Luc Fauchère、Godefridus Ignatius Tesser、Robert Schwyzer

  DOI：10.1002/hlca.19750580724

  日期：1975.11.5

  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].
• Diaz; Cazaubon; Demarne, European Journal of Medicinal Chemistry, 1985, vol. 20, # 3, p. 219 - 227
  作者：Diaz、Cazaubon、Demarne、et al.

  DOI：——

  日期：——