Boc-L-Arg-(Alloc)2-OH

• 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-L-Arg-(Alloc)2-OH
• 英文别名: (2S)-5-[bis(prop-2-enoxycarbonylamino)methylideneamino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoic acid
• 化学式: C₁₉H₃₀N₄O₈
• 分子量: 442.469
• InChiKey: GVBDFTCLBMDVGM-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  31
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  165
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Boc-L-Arg-(Alloc)2-OH 、 (R)-2-Amino-3-[(R)-2-amino-2-(4-phenylacetoxy-benzyloxycarbonyl)-ethyldisulfanyl]-propionic acid 4-phenylacetoxy-benzyl ester 在 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 作用下， 生成
  参考文献：
  名称：

  Synthesis and Membrane-Binding Properties of a Characteristic Lipopeptide from the Membrane-Anchoring Domain of Influenza Virus A Hemagglutinin

  摘要：

  On the trail of the influenza virus! Fluorescent-labeled lipopeptides, such as the characteristic S-palmitoylated partial structure from influenza virus hemagglutinin A, can be synthesized efficiently by employing a new enzymatic protecting-group technique in the key steps. Their binding to model membranes was determined in a kinetic assay, so leading to a first approximation of the membrane-anchoring ability of the corresponding lipopeptide motif in the parent protein.

  DOI：

  10.1002/1521-3773(20010119)40:2<369::aid-anie369>3.0.co;2-7
• 作为产物：
  描述：

  1H-pyrazole-N-allyloxycarbonyl-1-carboxamidine 在 sodium hydride 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 Boc-L-Arg-(Alloc)2-OH
  参考文献：
  名称：

  Total synthesis of miraziridine A and identification of its major reaction site for cathepsin B

  摘要：

  The synthesis of miraziridine A, a pentapeptide derivative isolated from marine sponge, and its truncated analogs has been achieved. To construct the backbone of miraziridine A, a side-chain-unprotected vinylogous arginine was condensed with an aziridine-containing fragment prepared by a conventional solid-phase procedure. An analog lacking the vinylogous arginine site showed comparable inhibitory activity with miraziridine A, whereas an analog lacking the aziridine site showed remarkably weak inhibitory activity for cathepsin B. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.06.082

文献信息

• Gothe, Rita; Seyfarth, Lydia; Schumann, Christina, Journal fur Praktische Chemie (Weinheim), 1999, vol. 341, # 4, p. 369 - 377
  作者：Gothe, Rita、Seyfarth, Lydia、Schumann, Christina、Agricola, Inge、Reissmann, Siegmund、Lifferth, Axel、Birr, Christian、Filatova, Magarita Pavlovna、Kritsky, Alexander、Kibirev, Vladimir

  DOI：——

  日期：——
• Synthesis and Antitumor Activity of Mechercharmycin A Analogues
  作者：Delia Hernández、Marta Altuna、Carmen Cuevas、Rosa Aligué、Fernando Albericio、Mercedes Álvarez

  DOI：10.1021/jm800513w

  日期：2008.9.25

  Several analogues of the cytotoxic thiopeptide IB-01211 or mechercharmycin A (1) have been synthesized. The cytotoxicity of 1 and the synthesized analogues were evaluated against a panel of three human tumor cell lines. Thiopeptide 1 and the most active derivatives 2 and 3c were chosen for further studies on effects on cell cycle progression and induction of apoptosis. Interestingly, the inhibition of cell division and activation of a programmed cell death by apoptosis were detected.
• Total synthesis of miraziridine A and identification of its major reaction site for cathepsin B
  作者：Hiroyuki Konno、Kanako Kubo、Hidefumi Makabe、Emi Toshiro、Naoyuki Hinoda、Kazuto Nosaka、Kenichi Akaji

  DOI：10.1016/j.tet.2007.06.082

  日期：2007.9

  The synthesis of miraziridine A, a pentapeptide derivative isolated from marine sponge, and its truncated analogs has been achieved. To construct the backbone of miraziridine A, a side-chain-unprotected vinylogous arginine was condensed with an aziridine-containing fragment prepared by a conventional solid-phase procedure. An analog lacking the vinylogous arginine site showed comparable inhibitory activity with miraziridine A, whereas an analog lacking the aziridine site showed remarkably weak inhibitory activity for cathepsin B. (C) 2007 Elsevier Ltd. All rights reserved.
• Synthesis and Membrane-Binding Properties of a Characteristic Lipopeptide from the Membrane-Anchoring Domain of Influenza Virus A Hemagglutinin
  作者：Frank Eisele、Jürgen Kuhlmann、Herbert Waldmann

  DOI：10.1002/1521-3773(20010119)40:2<369::aid-anie369>3.0.co;2-7

  日期：2001.1.19

  On the trail of the influenza virus! Fluorescent-labeled lipopeptides, such as the characteristic S-palmitoylated partial structure from influenza virus hemagglutinin A, can be synthesized efficiently by employing a new enzymatic protecting-group technique in the key steps. Their binding to model membranes was determined in a kinetic assay, so leading to a first approximation of the membrane-anchoring ability of the corresponding lipopeptide motif in the parent protein.