(SSS)-N(BzGly*ValNHOBn)3 | 197637-10-8

• 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: (SSS)-N(BzGly*ValNHOBn)3
• CAS: 197637-10-8
• 化学式: C₆₃H₇₂N₁₀O₁₂
• 分子量: 1161.32
• InChiKey: ATQHRRDKXJGHHB-ZOPNQXNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.72
• 重原子数：
  85.0
• 可旋转键数：
  30.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  292.83
• 氢给体数：
  9.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  (SSS)-N(BzGly*ValNHOBn)3 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以99%的产率得到(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：

  N-benzoyl-2-bromoglycine methyl ester 在 N-乙基吗啉 、 lithium hydroxide 、 氨 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 96.0h， 生成 (SSS)-N(BzGly*ValNHOBn)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