N,N-bis[2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]aminoacetic acid | 156939-63-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: N,N-bis[2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]aminoacetic acid
• 英文别名: bis(Fmoc-aminoethyl)-N-glycine；2-[bis[2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]amino]acetic acid
• CAS: 156939-63-8
• 化学式: C₃₆H₃₅N₃O₆
• 分子量: 605.69
• InChiKey: VOAULNVCTYOJJN-UHFFFAOYSA-N

物化性质

• 熔点：
  131-132 °C (decomp)
• 沸点：
  838.6±65.0 °C(Predicted)
• 密度：
  1.292±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  45
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  117
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  bis((9H-fluoren-9-yl)methyl) (12-(2-((3-((tert-butoxycarbonyl)amino)propyl)amino)-2-oxoethyl)-8,16-dioxo-3,6,18,21-tetraoxa-9,12,15-triazatricosane-1,23-diyl)dicarbamate 、 N,N-bis[2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]aminoacetic acid 在 哌啶 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以27%的产率得到
  参考文献：
  名称：

  Disulfide re-bridging reagents for single-payload antibody-drug conjugates

  摘要：

  四反应型二硫化物再桥接试剂 TetraDVP 能够高效合成含有单一有效载荷的抗体药物共轭物 (ADC)。

  DOI：

  10.1039/d3cc02980h
• 作为产物：
  描述：

  N-(芴甲氧羰基)甘氨酰氯 在 四(三苯基膦)钯 三正丁基氢锡 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 甲醇 、 溶剂黄146 为溶剂， 生成 N,N-bis[2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]aminoacetic acid
  参考文献：
  名称：

  通过用NaBH 3 CN还原Fmoc-氨基醛来形成双（Fmoc-氨基乙基）-N-甘氨酸衍生物

  摘要：

  描述了NaBH 3 CN还原Fmoc-氨基醛的意外结果。除了最初需要的产物Fmoc-Tyr（OtBu）-ψ（CH 2 NH）-Gly-OH，还从甘氨酸和Fmoc-4-t-丁氧基-酪氨酸中获得了少量的双缩合产物。从甘氨酸甲酯和Fmoc-甘氨酸，我们仅回收了还原的肽键等排体，但是从甘氨酸和Fmoc-甘氨酸，获得了双（Fmoc-氨基乙基）-N-甘氨酸作为主要产物。

  DOI：

  10.1016/0040-4039(94)88018-2

文献信息

• Design of New Bidentate Ligands Constructed of Two Hoechst 33258 Units for Discrimination of the Length of Two A₃T₃ Binding Motifs
  作者：Mikimasa Tanada、Saori Tsujita、Shigeki Sasaki

  DOI：10.1021/jo051836t

  日期：2006.1.1

  The aim of this study is to develop bidentate minor-groove binders that bind the double binding motifs cooperatively. The new bidentate ligands (1) have been designed by connecting two Hoechst 33258 units with a polyether linker for cooperative binding with two remote A(3)T(3) sites of DNA. The linker is introduced to the benzimidazole ring so that it is located at the convex side of the Hoechst unit. DNA binding affinity of the ligands was evaluated by measuring surface plasmon resonance (SPR), circular dichroism, and fluorescence spectra. Interestingly, the bidentate ligands (1) did not show affinity to DNA1 with a single A(3)T(3) motif but showed selective affinity to DNA2 with two A(3)T(3) motifs. The Long Bis-H (1L) having a long polyether linker showed specific binding to DNA2(6) with two A3T3 motifs separated by six nonbinding base pairs. The Long Bis-H (1L) has also shown specific binding to the three-way junction DNA4 with two A(3)T(3) motifs. This study has demonstrated that DNA with double binding motifs can be selectively recognized by the newly designed bidentate ligands.
• Formation of bis (Fmoc-amino ethyl)-N-glycine derivatives by reductive amination of Fmoc-amino aldehydes with NaBH3CN
  作者：Jean-Paul Salvi、Nadia Walchshofer、Joelle Paris

  DOI：10.1016/0040-4039(94)88018-2

  日期：1994.2

  amination of Fmoc-amino aldehydes by NaBH3CN are described. From glycine and Fmoc-4-t-Butoxy-tyrosinal, a small amount of double condensation product was obtained beside the initially desired product Fmoc-Tyr(OtBu)-ψ(CH2NH)-Gly-OH. From glycine methyl ester and Fmoc-glycinal, we only recovered the reduced peptide bond isostere, but from glycine and Fmoc-glycinal, bis(Fmoc-amino ethyl)-N-glycine was obtained

  描述了NaBH 3 CN还原Fmoc-氨基醛的意外结果。除了最初需要的产物Fmoc-Tyr（OtBu）-ψ（CH 2 NH）-Gly-OH，还从甘氨酸和Fmoc-4-t-丁氧基-酪氨酸中获得了少量的双缩合产物。从甘氨酸甲酯和Fmoc-甘氨酸，我们仅回收了还原的肽键等排体，但是从甘氨酸和Fmoc-甘氨酸，获得了双（Fmoc-氨基乙基）-N-甘氨酸作为主要产物。
• Disulfide re-bridging reagents for single-payload antibody-drug conjugates
  作者：Thomas A. King、Stephen J. Walsh、Mia Kapun、Thomas Wharton、Sona Krajcovicova、Melanie S. Glossop、David R. Spring

  DOI：10.1039/d3cc02980h

  日期：——

  A tetra-reactive disulfide re-bridging reagent, TetraDVP, enables the efficient synthesis of antibody-drug conjugates (ADCs) bearing a single payload.

  四反应型二硫化物再桥接试剂 TetraDVP 能够高效合成含有单一有效载荷的抗体药物共轭物 (ADC)。