H-D-Tyr-D-Lys-D-Gln-D-Cys-D-His-D-Lys-D-Lys-Gly-Gly-D-Lys-D-Lys-Gly-D-Ser-Gly-OH | 1078162-71-6

• 分子结构分类: 有机化合物 - 有机聚合物 - 多肽
• 英文名称: H-D-Tyr-D-Lys-D-Gln-D-Cys-D-His-D-Lys-D-Lys-Gly-Gly-D-Lys-D-Lys-Gly-D-Ser-Gly-OH
• 英文别名: 2-[[(2R)-2-[[2-[[(2R)-6-amino-2-[[(2R)-6-amino-2-[[2-[[2-[[(2R)-6-amino-2-[[(2R)-6-amino-2-[[(2R)-2-[[(2S)-2-[[(2R)-5-amino-2-[[(2R)-6-amino-2-[[(2R)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]hexanoyl]amino]-5-oxopentanoyl]amino]-3-sulfanylpropanoyl]amino]-3-(1H-imidazol-5-yl)propanoyl]amino]hexanoyl]amino]hexanoyl]amino]acetyl]amino]acetyl]amino]hexanoyl]amino]hexanoyl]amino]acetyl]amino]-3-hydroxypropanoyl]amino]acetic acid
• CAS: 1078162-71-6
• 化学式: C₆₄H₁₀₈N₂₂O₁₈S
• 分子量: 1505.76
• InChiKey: IQQBVMLUGSHKIO-DPOPDVEMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -10.4
• 重原子数：
  105
• 可旋转键数：
  56
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  685
• 氢给体数：
  25
• 氢受体数：
  26

反应信息

• 作为产物：
  描述：

  Fmoc-甘氨酸 、 N-alpha-芴甲氧羰基-N-epsilon-叔丁氧羰基-D-赖氨酸 、 Fmoc-O-叔丁基-D-丝氨酸 、 Fmoc-O-叔丁基-D-酪氨酸 、 N-芴甲氧羰基-N'-三苯甲基-D-组氨酸 、 N-Fmoc-S-三苯甲基-D-半胱氨酸 、 N-Fmoc-N'-三苯甲基-D-谷氨酰胺 在 Fmoc-Rink-amide (MBHA) resin 作用下， 生成 H-D-Tyr-D-Lys-D-Gln-D-Cys-D-His-D-Lys-D-Lys-Gly-Gly-D-Lys-D-Lys-Gly-D-Ser-Gly-OH
  参考文献：
  名称：

  A Novel Cell-Penetrating Peptide Sequence Derived by Structural Minimization of a Snake Toxin Exhibits Preferential Nucleolar Localization

  摘要：

  Structural simplification of a 42-residue venom peptide by N-to-C-terminal splicing led to two sequences [YKQCHKKG-GXKKGSG, where X = nil (1) or 6-aminohexanoyl (2)], both efficiently uptaken by HeLa cells and, most interestingly, specifically localized at the nucleolus. Retro-2 was uptaken less efficiently, but a single (His -> Ile) replacement recovered the translocation ability. None of the peptides were cytotoxic up to 100 mu M. Enantio-1 did not translocate, suggesting that peptide uptake was receptor-mediated.

  DOI：

  10.1021/jm8009475

文献信息

• A Novel Cell-Penetrating Peptide Sequence Derived by Structural Minimization of a Snake Toxin Exhibits Preferential Nucleolar Localization
  作者：Gandhi Rádis-Baptista、Beatriz G. de la Torre、David Andreu

  DOI：10.1021/jm8009475

  日期：2008.11.27

  Structural simplification of a 42-residue venom peptide by N-to-C-terminal splicing led to two sequences [YKQCHKKG-GXKKGSG, where X = nil (1) or 6-aminohexanoyl (2)], both efficiently uptaken by HeLa cells and, most interestingly, specifically localized at the nucleolus. Retro-2 was uptaken less efficiently, but a single (His -> Ile) replacement recovered the translocation ability. None of the peptides were cytotoxic up to 100 mu M. Enantio-1 did not translocate, suggesting that peptide uptake was receptor-mediated.