Boc-D-Lys(2-chloro-carbobenzoxy)-Ψ[(E)-CH=CH]-L-Ala-O-tBu | 359428-56-1

• 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: Boc-D-Lys(2-chloro-carbobenzoxy)-Ψ[(E)-CH=CH]-L-Ala-O-tBu
• 英文别名: tert-butyl (E,2R,5R)-9-[(2-chlorophenyl)methoxycarbonylamino]-2-methyl-5-[(2-methylpropan-2-yl)oxycarbonylamino]non-3-enoate
• CAS: 359428-56-1
• 化学式: C₂₇H₄₁ClN₂O₆
• 分子量: 525.085
• InChiKey: BTRRPJQCLQPBRX-WHAUSFDRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  36
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Boc-D-Lys(2-chloro-carbobenzoxy)-Ψ[(E)-CH=CH]-L-Ala-O-tBu 在 三氟乙酸 作用下， 生成 (E)-(2R,5R)-5-Amino-9-(2-chloro-benzyloxycarbonylamino)-2-methyl-non-3-enoic acid
  参考文献：
  名称：

  Synthesis and evaluation of pseudopeptide analogues of a specific CXCR4 inhibitor, T140: The insertion of an (E)-alkene dipeptide isostere into the βII′-turn moiety

  摘要：

  A 14-residue peptide, T140, strongly inhibits the T-cell line-tropic HIV-1 (X4-HIV-1) infection, since this peptide functions as a specific antagonist against a chemokine receptor, CXCR4. T140 takes an antiparallel beta-sheet structure with a type II' P-turn. In the present paper, we have designed and synthesized several T140 analogues in which an (E)-alkene dipeptide isostere was inserted into the type II' beta-turn moiety, as a bridging study to develop nonpeptidic CXCR4 inhibitors. It has been proven that the turn region of T140 can be replaced by the above surrogate with the maintenance of strong anti-HIV activity. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00041-0
• 作为产物：
  描述：

  二乙基膦酰基乙酸叔丁酯 在 吡啶 、 4-二甲氨基吡啶 、 sodium carbonate 、 N,N-二异丙基乙胺 、 lithium chloride 作用下， 以 甲醇 为溶剂， 生成 Boc-D-Lys(2-chloro-carbobenzoxy)-Ψ[(E)-CH=CH]-L-Ala-O-tBu
  参考文献：
  名称：

  Synthesis and evaluation of pseudopeptide analogues of a specific CXCR4 inhibitor, T140: The insertion of an (E)-alkene dipeptide isostere into the βII′-turn moiety

  摘要：

  A 14-residue peptide, T140, strongly inhibits the T-cell line-tropic HIV-1 (X4-HIV-1) infection, since this peptide functions as a specific antagonist against a chemokine receptor, CXCR4. T140 takes an antiparallel beta-sheet structure with a type II' P-turn. In the present paper, we have designed and synthesized several T140 analogues in which an (E)-alkene dipeptide isostere was inserted into the type II' beta-turn moiety, as a bridging study to develop nonpeptidic CXCR4 inhibitors. It has been proven that the turn region of T140 can be replaced by the above surrogate with the maintenance of strong anti-HIV activity. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00041-0

文献信息

• Synthesis and evaluation of pseudopeptide analogues of a specific CXCR4 inhibitor, T140: The insertion of an (E)-alkene dipeptide isostere into the βII′-turn moiety
  作者：Hirokazu Tamamura、Kenichi Hiramatsu、Kazuhide Miyamoto、Akane Omagari、Shinya Oishi、Hideki Nakashima、Naoki Yamamoto、Yoshihiro Kuroda、Terumichi Nakagawa、Akira Otaka、Nobutaka Fujii

  DOI：10.1016/s0960-894x(02)00041-0

  日期：2002.3

  A 14-residue peptide, T140, strongly inhibits the T-cell line-tropic HIV-1 (X4-HIV-1) infection, since this peptide functions as a specific antagonist against a chemokine receptor, CXCR4. T140 takes an antiparallel beta-sheet structure with a type II' P-turn. In the present paper, we have designed and synthesized several T140 analogues in which an (E)-alkene dipeptide isostere was inserted into the type II' beta-turn moiety, as a bridging study to develop nonpeptidic CXCR4 inhibitors. It has been proven that the turn region of T140 can be replaced by the above surrogate with the maintenance of strong anti-HIV activity. (C) 2002 Elsevier Science Ltd. All rights reserved.