Nα-Boc-Lys(Nε-2,4-Cl2Z) | 83038-58-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Nα-Boc-Lys(Nε-2,4-Cl2Z)
• 英文别名: N^α-Boc-Lys(N^ε-2,4-Cl2Z)；Boc-Lys(DCZ)-OH；N^α-tert-Butyloxycarbonyl-N^ε-2,6-dichlorbenzyloxycarbonyl-L-lysin
• CAS: 83038-58-8
• 化学式: C₁₉H₂₆Cl₂N₂O₆
• 分子量: 449.331
• InChiKey: CJOJVZNGTQXCBN-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.37
• 重原子数：
  29.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  113.96
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Nα-Boc-Lys(Nε-2,4-Cl2Z) 、 硝苯酚 在 N,N'-二环己基碳二亚胺 作用下， 以 吡啶 为溶剂， 生成 N^α-tert-Butyloxycarbonyl-N^ε-2,6-dichlorbenzyloxycarbonyl-L-lysin-o-nitrophenylester
  参考文献：
  名称：

  o-Nitrophenyl esters of tert-butyloxycarbonylamino acids and their application in the stepwise synthesis of peptide chains by a new technique

  摘要：

  DOI：

  10.1021/jo00960a027
• 作为产物：
  描述：

  2,6-二氯苄醇 在 sodium hydroxide 作用下， 以 1,4-二氧六环 、 苯 为溶剂， 反应 5.0h， 生成 Nα-Boc-Lys(Nε-2,4-Cl2Z)
  参考文献：
  名称：

  o-Nitrophenyl esters of tert-butyloxycarbonylamino acids and their application in the stepwise synthesis of peptide chains by a new technique

  摘要：

  DOI：

  10.1021/jo00960a027

文献信息

• Synthesis of Peptides Influencing Growth Hormone Release
  作者：Jan Hlaváček、Otto Smékal、Jan Pospíšek、Tomislav Barth

  DOI：10.1135/cccc19940707

  日期：——

  A solid phase peptide synthesis of 17 growth hormone (GH) releasing peptide analogues Ia - IIIc for their use in a pharmacological assay on GH release is described. While the linear peptide amides Ia - Ij were synthesized on p-methylbenzhydrylamine resin using Boc strategy, and cleaved by HF in the presence of scavengers the linear peptide amides Ik and Il were prepared on Merrifield benzyl ester type resin using Fmoc strategy and cleaved by ammonolysis. The deleted peptide amides IIa and IIb were obtained as by-products during HPLC purification of analogues Ic and Id. The linear precursors of cyclic peptides IIIa - IIIc were also prepared on Merrifield resin and cleaved under mild alkaline conditions. Their cyclization was performed in solution by diphenylphosphoryl azide.

  描述了一种用于生长激素（GH）释放肽类似物在GH释放药理试验中的固相肽合成，用于合成17种生长激素（GH）释放肽类似物 Ia - IIIc。线性肽酰胺 Ia - Ij 使用Boc策略在 p-甲基苯基亚胺树脂上合成，并在氢氟酸存在下裂解，而线性肽酰胺 Ik 和 Il 使用Fmoc策略在Merrifield苄酯型树脂上制备，并通过氨解裂解。在纯化类似物 Ic 和 Id 的HPLC过程中，删除的肽酰胺 IIa 和 IIb 作为副产物获得。环肽的线性前体 IIIa - IIIc 也在Merrifield树脂上制备，并在温和碱性条件下裂解。它们的环化是通过二苯基磷酸酰氮在溶液中进行的。
• Structure-activity studies of a novel bicyclic oxytocin antagonist
  作者：D. David Smith、Jirina Slaninova、Victor J. Hruby

  DOI：10.1021/jm00087a009

  日期：1992.5

  In this report, we describe structure-activity studies of the bicyclic oxytocin antagonist [Mpa1,cyclo(Glu4,Lys8)]oxytocin. The monocylic analogue [dPen1,Glu4,Lys8)]oxytocin was a weak oxytocin antagonist with a pA2 Value of 5.8 in the uterotonic assay. Bicyclization of this analogue yielded [dPen1,cyclo(Glu4,Lys8)]oxytocin, a potent antagonist of oxytocin in the uterotonic assay (pA2 8.74) with a potency 3 times greater than that of [Mpa1,cyclo(Glu4,Lys8)]oxytocin. [dPen1,cyclo(Glu4,Lys8)]oxytocin also was a weak antagonist in the pressor assay with a pA2 of 6.3. To establish if the potent antagonistic effects of these bicyclic compounds was because of the lactam ring or merely the result of obtaining an optimal degree of lipophilicity of the side chains in positions 4 and 8, we synthesized a series of analogues containing neutral and/or charged groups on these side chains. Monocyclic derivatives of [Mpa1,Gln4,Lys(CHO)8]oxytocin were moderate to weak agonists of oxytocin all following classical structure-activity profiles of oxytocin. The monocyclic derivatives of [dPen1,Gln4,Lys(CHO)8]oxytocin were antagonists of oxytocin which was attributed to the dPen1 substitution. However, the potency of all of these latter derivatives was at least 1 order of magnitude less than [dPen1,cyclo(Glu4,Lys8)]oxytocin. These results suggest that the potent antagonistic properties of the bicyclic analogues [Mpa1,cyclo(Glu4,Lys8)]oxytocin and [dPen1,cyclo(Glu4,Lys8)]oxytocin can be attributed to the effect of the lactam bridge on the conformational flexibility and topographical properties of the analogues, rendering them more favorable for binding to the receptor in such a manner as to prevent transduction of a biological response.