N,N',N''-{(SSS)-Nitrilotris[2-(benzoylamino)-1-oxo-2,1-ethanediyl]}tris(L-valine) | 197636-81-0

• 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: N,N',N''-{(SSS)-Nitrilotris[2-(benzoylamino)-1-oxo-2,1-ethanediyl]}tris(L-valine)
• CAS: 197636-81-0
• 化学式: C₄₂H₅₁N₇O₁₂
• 分子量: 845.907
• InChiKey: FFUJNMDPIYLZAR-FSJACQRISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.23
• 重原子数：
  61.0
• 可旋转键数：
  21.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  289.74
• 氢给体数：
  9.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  N,N',N''-{(SSS)-Nitrilotris[2-(benzoylamino)-1-oxo-2,1-ethanediyl]}tris(L-valine) 在 palladium on activated charcoal N-乙基吗啉 、 氢气 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 42.0h， 生成 (SSS)-N(BzGly*ValNHOH)3
  参考文献：
  名称：

  Tripodal Synthetic Peptide Bundles

  摘要：

  AbstractThe stereochemical course of the formation of the two diastereomers of trimethyl 2,2′,2″‐nitrilotris[2‐(benzoylamino)acetate], 2a and 2b, is described. The structures of both isomers were confirmed by X‐ray diffraction studies. Diastereomer 2b could be obtained in larger quantities by epimerisation of 2 a to 2 b with catalytical amounts of NaOMe. The (RRR/SSS)‐triester 2 b is a suitable template for the synthesis of tripodal peptide bundles. Saponification of 2 b yielded the C3‐symmetrical racemic triacid 4 b, which was coupled with amino acid methyl esters and dipeptide esters to give pseudo‐hexapeptides and pseudo‐nonapeptides, respectively. The resulting mixtures of diastereomers were easily separated by crystallisation. Their absolute configuration at the template unit (RRR or SSS) was established by means of the CD spectra. The pseudo‐hexapeptide (SSS)N(BzGly*ValOMe)3 (14) was saponified to yield the optically pure triacid (SSS)N(BzGly*ValOH)3 (23). Compound 23 is an ideally preorganised template for the production of longer tripodal peptides. This was illustrated by the synthesis of two pseudo‐pentadecapeptides. Peptide bundles with polar side chains (histidine and serine) or end groups (catechol or hydroxamate units) were synthesised by using the templates 4 b, 22 and 23 as anchors.

  DOI：

  10.1002/chem.19970030813
• 作为产物：
  描述：

  (RRR/SSS)-2,2',2''-Nitrilotris<2-(benzoylamino)acetic acid> 在 N-乙基吗啉 、 lithium hydroxide 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 36.0h， 生成 N,N',N''-{(SSS)-Nitrilotris[2-(benzoylamino)-1-oxo-2,1-ethanediyl]}tris(L-valine)
  参考文献：
  名称：

  Tripodal Synthetic Peptide Bundles

  摘要：

  AbstractThe stereochemical course of the formation of the two diastereomers of trimethyl 2,2′,2″‐nitrilotris[2‐(benzoylamino)acetate], 2a and 2b, is described. The structures of both isomers were confirmed by X‐ray diffraction studies. Diastereomer 2b could be obtained in larger quantities by epimerisation of 2 a to 2 b with catalytical amounts of NaOMe. The (RRR/SSS)‐triester 2 b is a suitable template for the synthesis of tripodal peptide bundles. Saponification of 2 b yielded the C3‐symmetrical racemic triacid 4 b, which was coupled with amino acid methyl esters and dipeptide esters to give pseudo‐hexapeptides and pseudo‐nonapeptides, respectively. The resulting mixtures of diastereomers were easily separated by crystallisation. Their absolute configuration at the template unit (RRR or SSS) was established by means of the CD spectra. The pseudo‐hexapeptide (SSS)N(BzGly*ValOMe)3 (14) was saponified to yield the optically pure triacid (SSS)N(BzGly*ValOH)3 (23). Compound 23 is an ideally preorganised template for the production of longer tripodal peptides. This was illustrated by the synthesis of two pseudo‐pentadecapeptides. Peptide bundles with polar side chains (histidine and serine) or end groups (catechol or hydroxamate units) were synthesised by using the templates 4 b, 22 and 23 as anchors.

  DOI：

  10.1002/chem.19970030813

文献信息

• Zinc(II) complexes of tripodal peptides mimicking the zinc(II)-coordination structure of carbonic anhydrase
  作者：Ulrike Herr、Werner Spahl、Gunter Trojandt、Wolfgang Steglich、Florian Thaler、Rudi van Eldik

  DOI：10.1016/s0968-0896(98)00180-1

  日期：1999.5

  synthesized and were shown to form stable zinc(II) complexes. Their NMR and mass spectra indicate a structure that is analogous to the active center of carbonic anhydrase. Both the ligands and the zinc complexes were titrated potentiometrically in order to obtain the pKa values for the coordinated water of the zinc complexes; due to the low solubility of the complexes only estimates could be obtained.

  具有组氨酸侧链的两个新的三脚架肽配体已经合成，并显示形成稳定的锌（II）配合物。它们的NMR和质谱表明其结构类似于碳酸酐酶的活性中心。用电位滴定法对配体和锌络合物进行滴定，以获得锌络合物配位水的pKa值。由于复合物的低溶解度，只能得到估计值。