A9K | 187243-19-2

• 分子结构分类: 有机化合物 - 有机聚合物 - 多肽
• 英文名称: A9K
• 英文别名: H-Ala-Ala-Ala-Ala-Ala-Ala-Ala-Ala-Ala-Lys-OH；(2S)-6-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-aminopropanoyl]amino]propanoyl]amino]propanoyl]amino]propanoyl]amino]propanoyl]amino]propanoyl]amino]propanoyl]amino]propanoyl]amino]propanoyl]amino]hexanoic acid
• CAS: 187243-19-2
• 化学式: C₃₃H₅₉N₁₁O₁₁
• 分子量: 785.899
• InChiKey: DGJBBMVAQIPPSB-XBIOHXSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.5
• 重原子数：
  55
• 可旋转键数：
  23
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  351
• 氢给体数：
  12
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  A9K 、 Cucurbituril 生成
  参考文献：
  名称：

  Host–Guest Chemistry in the Gas Phase: Selected Fragmentations of CB[6]–Peptide Complexes at Lysine Residues and Its Utility to Probe the Structures of Small Proteins

  摘要：

  利用电喷雾质谱法（ESI-MS）研究了葫芦[6]脲（CB[6]）与肽之间的气相主-客化学反应。CB[6] 对与肽中的赖氨酸残基相互作用表现出很高的偏好，从而形成 CB[6] - 肽复合物。肽的碰撞活化 CB[6] 复合物在 m/z 549.2 处产生一个共同的高选择性碎片产物，对应于 5-亚氨基戊基铵（5IPA）的双电荷 CB[6] 复合物。这一过程包括形成一个内部亚氨基离子，该亚氨基离子从一个 y 型离子进一步分裂成一个 a 型离子，由此产生的 5IPA 离子穿过 CB[6] 复合物。研究人员对大量肽进行了研究，以检验所观察到的 CB 独特的主宾化学反应的普遍性[6]。利用泛素的 CB[6] 复合物证明了它在探测蛋白质结构方面的潜在用途。低能碰撞诱导解离产生了 CB[6] 复合物片段，进一步的 MSn 光谱揭示了 CB[6] 结合位点的细节，使我们能够推断出溶液阶段的蛋白质结构。我们利用密度泛函理论计算对观察到的反应机制和能量进行了评估。

  DOI：

  10.1021/ac201854a
• 作为产物：
  描述：

  Fmoc-L-丙氨酸 、 N-alpha-芴甲氧羰基-N-epsilon-叔丁氧羰基-L-赖氨酸 在 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 A9K
  参考文献：
  名称：

  Antibacterial Activities of Short Designer Peptides: a Link between Propensity for Nanostructuring and Capacity for Membrane Destabilization

  摘要：

  Amphiphilic peptides A(3)K, A(6)K and A(9)K displayed an increasing propensity for nanoaggregation with increasing the size of hydrophobic alanine moiety, and the size and shape of the aggregates showed a steady transition from loose peptide stacks formed by A(3)K long nanofibers by A(6)K, to short and narrow nanorods by A(9)K This size and shape transition was broadly consistent with the trend predicted from interfacial packing and curvature change if these peptide surfactants were treated as conventional surfactants The antibacterial capacity, defined by the killing of percentage of bacteria in a given time and peptide concentration, showed a strong correlation to peptide hydrophobicity, evident from both microscopic and fluorescence imaging studies For A(9)K, the power for membrane permeation and bacterial clustering intensified with peptide concentration and incubation time These results thus depict it positive correlation between the propensity for self-assembly of the peptides, their membrane penetration power, and bactericidal capacity Although the exposure of A(9)K to a preformed DPPC membrane bilayer showed little structural disturbance. the same treatment to the preformed DPPG membrane bilayer led to substantial disruption of model membrane structure, a trend entirely consistent with the high selectivity observed from membrane hemolytic studies.

  DOI：

  10.1021/bm901130u

文献信息

• Host–Guest Chemistry in the Gas Phase: Selected Fragmentations of CB[6]–Peptide Complexes at Lysine Residues and Its Utility to Probe the Structures of Small Proteins
  作者：Sung Woo Heo、Tae Su Choi、Kyung Man Park、Young Ho Ko、Seung Bin Kim、Kimoon Kim、Hugh I. Kim

  DOI：10.1021/ac201854a

  日期：2011.10.15

  The gas phase host–guest chemistry between cucurbit[6]uril (CB[6]) and peptide is investigated using electrospray ionization mass spectrometry (ESI-MS). CB[6] exhibits a high preference to interacting with a Lys residue in a peptide forming a CB[6]–peptide complex. Collisionally activated CB[6] complexes of peptides yield a common highly selective fragment product at m/z 549.2, corresponding to the doubly charged CB[6] complex of 5-iminiopentylammonium (5IPA). The process involves the formation of an internal iminium ion, which results from further fragments to an a-type ion from a y-type ion, and the resulting 5IPA ion threads through CB[6]. Numerous peptides are investigated to test the generality of the observed unique host–guest chemistry of CB[6]. Its potential utility in probing protein structures is demonstrated using CB[6] complexes of ubiquitin. Low-energy collision induced dissociation yields CB[6] complex fragments, and further MSn spectra reveal details of the CB[6] binding sites, which allow us to deduce the protein structure in the solution phase. The mechanisms and energetics of the observed reactions are evaluated using density functional theory calculations.

  利用电喷雾质谱法（ESI-MS）研究了葫芦[6]脲（CB[6]）与肽之间的气相主-客化学反应。CB[6] 对与肽中的赖氨酸残基相互作用表现出很高的偏好，从而形成 CB[6] - 肽复合物。肽的碰撞活化 CB[6] 复合物在 m/z 549.2 处产生一个共同的高选择性碎片产物，对应于 5-亚氨基戊基铵（5IPA）的双电荷 CB[6] 复合物。这一过程包括形成一个内部亚氨基离子，该亚氨基离子从一个 y 型离子进一步分裂成一个 a 型离子，由此产生的 5IPA 离子穿过 CB[6] 复合物。研究人员对大量肽进行了研究，以检验所观察到的 CB 独特的主宾化学反应的普遍性[6]。利用泛素的 CB[6] 复合物证明了它在探测蛋白质结构方面的潜在用途。低能碰撞诱导解离产生了 CB[6] 复合物片段，进一步的 MSn 光谱揭示了 CB[6] 结合位点的细节，使我们能够推断出溶液阶段的蛋白质结构。我们利用密度泛函理论计算对观察到的反应机制和能量进行了评估。
• Antibacterial Activities of Short Designer Peptides: a Link between Propensity for Nanostructuring and Capacity for Membrane Destabilization
  作者：Cuixia Chen、Fang Pan、Shengzhong Zhang、Jing Hu、Meiwen Cao、Jing Wang、Hai Xu、Xiubo Zhao、Jian R. Lu

  DOI：10.1021/bm901130u

  日期：2010.2.8

  Amphiphilic peptides A(3)K, A(6)K and A(9)K displayed an increasing propensity for nanoaggregation with increasing the size of hydrophobic alanine moiety, and the size and shape of the aggregates showed a steady transition from loose peptide stacks formed by A(3)K long nanofibers by A(6)K, to short and narrow nanorods by A(9)K This size and shape transition was broadly consistent with the trend predicted from interfacial packing and curvature change if these peptide surfactants were treated as conventional surfactants The antibacterial capacity, defined by the killing of percentage of bacteria in a given time and peptide concentration, showed a strong correlation to peptide hydrophobicity, evident from both microscopic and fluorescence imaging studies For A(9)K, the power for membrane permeation and bacterial clustering intensified with peptide concentration and incubation time These results thus depict it positive correlation between the propensity for self-assembly of the peptides, their membrane penetration power, and bactericidal capacity Although the exposure of A(9)K to a preformed DPPC membrane bilayer showed little structural disturbance. the same treatment to the preformed DPPG membrane bilayer led to substantial disruption of model membrane structure, a trend entirely consistent with the high selectivity observed from membrane hemolytic studies.