N^ω,N^ω-bis(benzyloxycarbonyl)-N^α-Fmoc-D-arginine | 910056-53-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: N^ω,N^ω-bis(benzyloxycarbonyl)-N^α-Fmoc-D-arginine
• 英文别名: Fmoc-D-Arg(Z,Z)；Fmoc-D-Arg(Z)2-OH；(2R)-5-[bis(phenylmethoxycarbonylamino)methylideneamino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)pentanoic acid
• CAS: 910056-53-0
• 化学式: C₃₇H₃₆N₄O₈
• 分子量: 664.715
• InChiKey: SLWMVWWEOHTNTR-JGCGQSQUSA-N

物化性质

• 熔点：
  158-159 °C
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  49
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  N^α-Fmoc-N^α-methylglutamine 、 N^ω,N^ω-bis(benzyloxycarbonyl)-N^α-Fmoc-D-arginine 、 FMOC-N-甲基-L-丙氨酸 、 芴甲氧羰基-L-苏氨酸 以26%的产率得到callipeltin E
  参考文献：
  名称：

  Solid-Phase Synthesis and Configurational Reassigment of Callipeltin E. Implications for the Structures of Callipeltins A and B

  摘要：

  Two possible isomers of the natural product callipeltin E (1, 5) were synthesized by using an Fmoc-based solid-phase strategy in 7 steps, in 20% and 26% overall yields, respectively. The H-1 NMR spectrum of synthetic 5 correlated closely with that of the natural product, whereas that of 1 did not, providing confirmation of the configurational reassignment of the N-terminal residue of callipeltin E as D-allothreonine. This result strongly implies that the corresponding residue in the closely related cyclic depsipeptides callipeltins A and B should also be considered a D-allothreonine residue.

  DOI：

  10.1021/jo060351h
• 作为产物：
  描述：

  Boc-D-Arg(Cbz2)-OH 在 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 1.5h， 生成 N^ω,N^ω-bis(benzyloxycarbonyl)-N^α-Fmoc-D-arginine
  参考文献：
  名称：

  Solid-Phase Synthesis and Configurational Reassigment of Callipeltin E. Implications for the Structures of Callipeltins A and B

  摘要：

  Two possible isomers of the natural product callipeltin E (1, 5) were synthesized by using an Fmoc-based solid-phase strategy in 7 steps, in 20% and 26% overall yields, respectively. The H-1 NMR spectrum of synthetic 5 correlated closely with that of the natural product, whereas that of 1 did not, providing confirmation of the configurational reassignment of the N-terminal residue of callipeltin E as D-allothreonine. This result strongly implies that the corresponding residue in the closely related cyclic depsipeptides callipeltins A and B should also be considered a D-allothreonine residue.

  DOI：

  10.1021/jo060351h

文献信息

• 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.
• Solid-Phase Synthesis and Configurational Reassigment of Callipeltin E. Implications for the Structures of Callipeltins A and B
  作者：Selçuk Çalimsiz、Ángel I. Morales Ramos、Mark A. Lipton

  DOI：10.1021/jo060351h

  日期：2006.8.1

  Two possible isomers of the natural product callipeltin E (1, 5) were synthesized by using an Fmoc-based solid-phase strategy in 7 steps, in 20% and 26% overall yields, respectively. The H-1 NMR spectrum of synthetic 5 correlated closely with that of the natural product, whereas that of 1 did not, providing confirmation of the configurational reassignment of the N-terminal residue of callipeltin E as D-allothreonine. This result strongly implies that the corresponding residue in the closely related cyclic depsipeptides callipeltins A and B should also be considered a D-allothreonine residue.