Boc-Phe-Phe-OEt | 66714-00-9

• 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: Boc-Phe-Phe-OEt
• 英文别名: ethyl (tert-butoxycarbonyl)-L-phenylalanyl-L-phenylalaninate；ethyl (2S)-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]amino]-3-phenylpropanoate
• CAS: 66714-00-9
• 化学式: C₂₅H₃₂N₂O₅
• 分子量: 440.539
• InChiKey: CYHLFXGWIGRSRD-SFTDATJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Boc-Phe-Phe-OEt 在 吡啶 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.5h， 生成 ethyl picolinoyl-L-phenylalanyl-L-phenylalaninate
  参考文献：
  名称：

  钴催化的氨基酸 C(sp2)-H 羰基化使用吡啶甲酰胺作为无痕导向基团

  摘要：

  在此，我们报告了一种基于廉价钴 (II) 盐催化剂的氨基酸衍生物C(sp 2 )-H 羰基化的有效方案。羰基化是使用吡啶甲酰胺作为无痕导向基团、CO (1 atm) 作为羰基源和 Co(dpm) 2作为催化剂来完成的。广泛的带有不同官能团的苯丙氨酸衍生物是可以耐受的。此外，该方法可成功应用于短肽的 C(sp 2 )-H 羰基化，从而允许进行肽后期羰基化。

  DOI：

  10.1021/acs.orglett.1c00660
• 作为产物：
  描述：

  BOC-L-苯丙氨酸 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 3.05h， 生成 Boc-Phe-Phe-OEt
  参考文献：
  名称：

  Efficient and Highly Selective Copper(II) Transport across a Bulk Liquid Chloroform Membrane Mediated by Lipophilic Dipeptides

  摘要：

  Several structurally simple N-monoalkylated and -dialkylated dipeptides made of alpha-amino acids Gly, Phe, and Leu, 1-11, were synthesized and investigated as carriers for the transport of Cu(II), Zn(II), and Ni(II) from an aqueous pH = 5.6 buffer source to a 0.1 M HCl receiving phase across a bulk chloroform membrane. The proton-driven translocation was followed during the process by analyzing the metal ion concentrations in the three phases. The transport efficiency depends on the ease of formation of a neutral complex with Cu(II) (the peptide group and carboxylic acid being deprotonated) at the source-chloroform interface and on that of its disruption by protonation at the receiving phase: the carrier's Lipophilicity favors the metal ion uptake and not the release. By modulating the length of the N-alkyl chains and the hydrophobicity of the dipeptide moiety, a quite remarkable transport efficiency was observed for Cu(II), in most cases superior to that of the industrial extractant Kelex 100. Moreover, using L,L- and L,D-N-octyl-PheLeu as carriers, remarkable diastereomeric effects were observed in the rate of uptake and release of Cu(II) ion although the differences mutually compensate in the overall transport rate. Under the conditions used the carriers are much less effective in the translocation of Zn(II) and Ni(II) and their transport efficiency drops dramatically in the presence of Cu(II), the latter being favored by factors of 1.2 x 10(3) and > 10(4), respectively. Such very high selectivities depend on the fact that only Cu(II) among other transition metal ions Can form neutral complexes at the pH value of the source phase.

  DOI：

  10.1021/jo9703257

文献信息

• Novel somatostatin analogue
  申请人：Shiraimatsu Shingaku Co., Ltd.

  公开号：US04261885A1

  公开（公告）日：1981-04-14

  Novel somatostatin analogs exhibiting high activity in inhibiting insulin glucagon and growth hormone secretion are depicted by the formula: ##STR1## and pharmaceutically acceptable acid addition salts thereof.

  描述了一些新型生长抑素类似物，其化学式为：##STR1##，在抑制胰岛素、胰高血糖素和生长激素分泌方面具有很高的活性，以及其药学上可接受的酸盐衍生物。
• Structures of L-phenylalanine dimers, N-(tert-butoxycarbonyl)-L-phenylalanyl-L-phenylalanine benzyl ester (Boc-Phe-Phe-OBzl) and L-phenylalanyl-L-phenylanine ethyl ester trifluoroacetate (Phe-Phe-OEt.Tfa)
  作者：O. Yamashita、Y. Kato、T. Yamane、T. Ashida

  DOI：10.1107/s0567740882009522

  日期：1982.10.15
• Use of Di‐<i>tert</i>‐butyl‐dicarbonate Both as a Protecting and Activating Group in the Synthesis of Dipeptides
  作者：S. Jhaumeer Laulloo、A. Khodaboccus、U. Hemraz、S. Sunnassee

  DOI：10.1080/00397910701575202

  日期：2007.12

  Amide formation from amino acids was achieved in an easy and convenient one-pot procedure using di-tert-butyl dicarbonate both as a protecting and an activating agent. A number of dipeptides have been synthesized in good yields.