Fmoc-D-alloThr(THP) | 918530-99-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: Fmoc-D-alloThr(THP)
• 英文别名: (2R,3R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(oxan-2-yloxy)butanoic acid
• CAS: 918530-99-1
• 化学式: C₂₄H₂₇NO₆
• 分子量: 425.481
• InChiKey: BSOWHWUPGMSWJV-WWFGYZFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  94.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N^ω,N^ω-bis(benzyloxycarbonyl)-N^α-Fmoc-D-arginine 、 Fmoc-D-alloThr(THP) 、 H-D-Tyr(Bn)-O-allyl 、 Fmoc-L-亮氨酸 、 alkaline earth salt of/the/ methylsulfuric acid 、 alkaline earth salt of/the/ methylsulfuric acid 以2.6 mg的产率得到desmethoxycallipeltin B
  参考文献：
  名称：

  Synthesis and cytotoxicity of desmethoxycallipeltin B: Lack of a quinone methide for the cytotoxicity of callipeltin B

  摘要：

  The desmethoxy analogue of the cytotoxic, cyclic depsipeptide callipeltin B was synthesized to evaluate the role of its beta-MeOTyr residue. The IC50 of desmethoxycallipeltin B, in which the beta-MeOTyr residue was replaced by D-Tyr, against HeLa cells was found to be 128 +/- 10 mu M in an MTT assay, compared to 98 5 mu M for the natural product itself. The roughly comparable cytotoxicities suggest that the cytotoxicity of callipeltin B does not arise through the formation of a quinone methide intermediate. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.07.003
• 作为产物：
  描述：

  芴甲氧羰基-L-苏氨酸 在 四(三苯基膦)钯 、 苯硅烷 、 4-甲基苯磺酸吡啶 、 甲基三辛基氯化铵 、 碳酸氢钠 作用下， 以 二氯甲烷 、 水 、 1,2-二氯乙烷 为溶剂， 反应 27.75h， 生成 Fmoc-D-alloThr(THP)
  参考文献：
  名称：

  Callipeltin B的固相全合成及结构证明

  摘要：

  细胞毒性、环状七肽、天然产物 callipeltin B 在固相载体上合成，总产率为 15%。三种合成异构体的 1H NMR 谱与 callipeltin B 的 1H NMR 谱的比较证实其苏氨酸残基的构型重新分配为 d-别苏氨酸，并将其 β-甲氧基酪氨酸残基的构型分配为 (2R,3R)。

  DOI：

  10.1021/ja0666250

文献信息

• Solid-Phase Total Synthesis and Structure Proof of Callipeltin B
  作者：Ravi Krishnamoorthy、Leslie D. Vazquez-Serrano、Jeffrey A. Turk、Jennifer A. Kowalski、Alan G. Benson、Nneka T. Breaux、Mark A. Lipton

  DOI：10.1021/ja0666250

  日期：2006.12.1

  The cytotoxic, cyclic heptadepsipeptide, natural product callipeltin B was synthesized on a solid-phase support in 15% overall yield. Comparison of the 1H NMR spectra of three synthetic isomers with those of callipeltin B confirmed the configurational reassignment of its threonine residues as d-allothreonine and the assignment of the configuration of its beta-methoxytyrosine residue as (2R,3R).

  细胞毒性、环状七肽、天然产物 callipeltin B 在固相载体上合成，总产率为 15%。三种合成异构体的 1H NMR 谱与 callipeltin B 的 1H NMR 谱的比较证实其苏氨酸残基的构型重新分配为 d-别苏氨酸，并将其 β-甲氧基酪氨酸残基的构型分配为 (2R,3R)。
• Synthesis and cytotoxicity of desmethoxycallipeltin B: Lack of a quinone methide for the cytotoxicity of callipeltin B
  作者：Ravi Krishnamoorthy、Brooke L. Richardson、Mark A. Lipton

  DOI：10.1016/j.bmcl.2007.07.003

  日期：2007.9

  The desmethoxy analogue of the cytotoxic, cyclic depsipeptide callipeltin B was synthesized to evaluate the role of its beta-MeOTyr residue. The IC50 of desmethoxycallipeltin B, in which the beta-MeOTyr residue was replaced by D-Tyr, against HeLa cells was found to be 128 +/- 10 mu M in an MTT assay, compared to 98 5 mu M for the natural product itself. The roughly comparable cytotoxicities suggest that the cytotoxicity of callipeltin B does not arise through the formation of a quinone methide intermediate. (c) 2007 Elsevier Ltd. All rights reserved.