H-Lys(BOC)-Gly-OMe | 45265-57-4

• 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: H-Lys(BOC)-Gly-OMe
• 英文别名: methyl 2-[[(2S)-2-amino-6-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoyl]amino]acetate
• CAS: 45265-57-4
• 化学式: C₁₄H₂₇N₃O₅
• 分子量: 317.385
• InChiKey: CMBLZHYCAYCVFU-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  22
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  120
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  H-Lys(BOC)-Gly-OMe 在 sodium hydroxide 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 49.0h， 生成 Z-Pro-Lys(BOC)-Gly-OH
  参考文献：
  名称：

  Modified di- and tripeptides of the C-terminal portion of oxytocin and vasopressin as possible cognition activation agents

  摘要：

  A number of peptides and modified peptides were synthesized and studied for their ability to reverse electroconvulsive shock-induced amnesia in rodents. A few of these peptides were selected for secondary evaluation in tests of short-term memory in rats and aged rhesus monkeys. A number of the peptides and modified peptides were active in the amnesia reversal test. In selected secondary tests, however, the chosen compounds failed to show significant activity in enhancing memory. New methods for preparing methyleneamino and methyleneoxy isosteres of peptides are reported. Other modified peptides also included methylenethio, methylenesulfonyl, and ethylene isosteres in place of the normal peptide amide bond.

  DOI：

  10.1021/jm00156a012
• 作为产物：
  描述：

  Z-Lys(BOC)-Gly-OMe 在 palladium on activated charcoal 氢气 、 柠檬酸 作用下， 以 甲醇 为溶剂， 反应 18.0h， 生成 H-Lys(BOC)-Gly-OMe
  参考文献：
  名称：

  Modified di- and tripeptides of the C-terminal portion of oxytocin and vasopressin as possible cognition activation agents

  摘要：

  A number of peptides and modified peptides were synthesized and studied for their ability to reverse electroconvulsive shock-induced amnesia in rodents. A few of these peptides were selected for secondary evaluation in tests of short-term memory in rats and aged rhesus monkeys. A number of the peptides and modified peptides were active in the amnesia reversal test. In selected secondary tests, however, the chosen compounds failed to show significant activity in enhancing memory. New methods for preparing methyleneamino and methyleneoxy isosteres of peptides are reported. Other modified peptides also included methylenethio, methylenesulfonyl, and ethylene isosteres in place of the normal peptide amide bond.

  DOI：

  10.1021/jm00156a012

文献信息

• Distinctive Nucleic Acid Recognition by Lysine-Embedded Phenanthridine Peptides
  作者：Josipa Matić、Patryciusz Piotrowski、Lucija Vrban、Renata Kobetić、Robert Vianello、Ivona Jurić、Ivana Fabijanić、Margareta Pernar Kovač、Anamaria Brozovic、Ivo Piantanida、Carsten Schmuck、Marijana Radić Stojković

  DOI：10.3390/ijms25094866

  日期：——

  Three new phenanthridine peptide derivatives (19, 22, and 23) were synthesized to explore their potential as spectrophotometric probes for DNA and RNA. UV/Vis and circular dichroism (CD) spectra, mass spectroscopy, and computational analysis confirmed the presence of intramolecular interactions in all three compounds. Computational analysis revealed that compounds alternate between bent and open conformations

  合成了三种新的菲啶肽衍生物（19、22 和 23），以探索它们作为 DNA 和 RNA 分光光度探针的潜力。紫外/可见光和圆二色性 (CD) 光谱、质谱和计算分析证实所有三种化合物都存在分子内相互作用。计算分析表明，化合物在弯曲构象和开放构象之间交替，突出了后者对成功的多核苷酸识别的关键影响。与含有两个甘氨酸的化合物 (19) 相比，在两种区域异构体 (22, 23) 中用赖氨酸取代一个甘氨酸可产生更强的与 DNA 和 RNA 的结合相互作用，从而强调了赖氨酸的重要性。赖氨酸更接近菲啶环（23）的区域异构体表现出与非交替AT和ATT多核苷酸的双重选择性荧光响应，并诱导从AT双链体形成三链体。与 AT 和 ATT 多核苷酸相互作用获得的最佳结合常数 (K) 值为 2.5 × 107 M−1。此外，除了区分不同类型的 ds-DNA 和 ds-RNA 之外，同一化合物还可以通过不同的诱导 CD 信号识别富含