1-(1-(1-(N-(N-L-缬氨酰-L-组氨酰)-L-亮氨酰)-L-脯氨酰)-L-脯氨酰)-L-脯氨酸 | 121322-14-3

• 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
• 中文名称: 1-(1-(1-(N-(N-L-缬氨酰-L-组氨酰)-L-亮氨酰)-L-脯氨酰)-L-脯氨酰)-L-脯氨酸
• 英文名称: Val-His-Leu-Pro-Pro-Pro
• 英文别名: H-Val-His(H)-Leu-Pro-Pro-Pro-OH；L-Proline, 1-(1-(1-(N-(N-L-valyl-L-histidyl)-L-leucyl)-L-prolyl)-L-prolyl)-；(2S)-1-[(2S)-1-[(2S)-1-[(2S)-2-[[(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-3-(1H-imidazol-5-yl)propanoyl]amino]-4-methylpentanoyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carboxylic acid
• CAS: 121322-14-3
• 化学式: C₃₂H₅₀N₈O₇
• 分子量: 658.798
• InChiKey: VRBRSQUJTJSJCL-FRSCJGFNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  47
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  211
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 哌啶 、 乙二胺四乙酸 、 三氟乙酸 作用下， 生成 1-(1-(1-(N-(N-L-缬氨酰-L-组氨酰)-L-亮氨酰)-L-脯氨酰)-L-脯氨酰)-L-脯氨酸
  参考文献：
  名称：

  Convergent Solid Phase Peptide Synthesis: An Efficient Approach to the Synthesis of Highly Repetitive Protein Domains

  摘要：

  Convergent solid phase peptide synthesis is a straightforward approach to the synthesis of protein domains with repetitive structures. The peptide H-(Val-His-Leu-Pro-Pro-Pro)(8)-OH corresponding to the N-terminal domain of gamma-zein has been synthesized using the protected segment Fmoc-(Val-His(Trt)-Leu-Pro-Pro-Pro)-OH as synthetic precursor. Solid phase repetitive coupling of the segment was achieved effectively using a synthetic protocol centered on the use of the new 7-aza-1-hydroxybenzotriazole-based reagents HATU and HOAt. The protected peptide segment Fmoc-Val-His(Trt)-Leu-Pro-Pro-Pro-OH was synthesized on a solid-phase using a combination of the base-labile Fmoc group for the alpha-amino protection, the acid-labile trityl group for the protection of the side-chain of histidine, and the highly acid-labile 4-(4-(hydroxymethyl)-3-methoxyphenoxy)butyric acid (HMPB) as handle, which allows the cleavage of the protected segment from the resin by treatment with 1% TFA in CH2Cl2 with complete retention of the amino acid side-chain protecting groups. This approach also allows the same peptide sequence at different levels of protection to be obtained by varying the cleavage program used and demonstrates that the versatile HMPB handle is completely compatible with the use of the trityl group for protection of the side-chain of histidine. The use of a small quantity of pyridine in the purification of this protected peptide by RPMPLC does not affect the Fmoc group and avoids premature imidazole detritylation. Finally, the general synthetic strategy described in this paper avoids the severe problems previously reported on the synthesis of these highly repetitive structures as demonstrated by a careful analysis of the target compounds by cation-exchange HPLC and electrospray MS.

  DOI：

  10.1021/jo00128a033

文献信息

• USE OF PEPTIDES AS PENETRATING CELL CARRIERS
  申请人：Universidad de Barcelona

  公开号：EP1724280A1

  公开（公告）日：2006-11-22

  The invention relates to compounds having formula (I) or the biologically- or pharmaceutically-acceptable salts thereof which are used as penetrating cell carriers. According to formula (I), Val is L-Val or D-Val; Arg is L-Arg, D-Arg or L-(N-methyl)Arg; Pro is L-Pro or D-Pro; Leu is L-Leu or D-Leu; x is an integer of between 1 and 20, preferably 3; L1 and L2 are chemical linkers; M1 and M2 are pharmaceutically- and/or biologically-active groups; and the linkage between L1 and M1 and the linkage between L2 and M2 are of any known chemical nature, including covalent and ionic. Compared to other previously-described carrier peptides, said novel family offers many advantages including its non-viral origin, amphipathic character, water solubility and the absence of a cytotoxic effect at high concentrations. M1-L1-(Val-Arg-Leu-Pro-Pro-Pro)x-L2-M2 (I)

  本发明涉及具有式（I）的化合物或其生物或药学上可接受的盐类，可用作渗透性细胞载体。根据式（I），Val 是 L-Val 或 D-Val；Arg 是 L-Arg、D-Arg 或 L-（N-甲基）Arg；Pro 是 L-Pro 或 D-Pro；Leu 是 L-Leu 或 D-Leu；x 是 1 到 20 之间的整数，最好是 3；L1 和 L2 是化学连接体；M1 和 M2 是药学和/或生物活性基团；L1 和 M1 之间的连接以及 L2 和 M2 之间的连接具有任何已知的化学性质，包括共价和离子。与之前描述的其他载体肽相比，上述新型家族具有许多优点，包括非病毒来源、两性特性、水溶性和高浓度下无细胞毒性效应。M1-L1-(Val-Arg-Leu-Pro-Pro-Pro)x-L2-M2 (I)
• Peptides as cell penetrating carriers
  申请人：Lledo Ernest Giralt

  公开号：US20090036363A1

  公开（公告）日：2009-02-05

  Compounds of formula (I) or their pharmaceutically or biologically acceptable salts are useful as cell penetrating carriers. According to formula (I), below, Val is L-Val or D-Val; Arg is L-Arg, D-Arg or L-(N-methyl)Arg; Pro is L-Pro or D-Pro; Leu is L-Leu or D-Leu; x is an integer from 1 to 20, preferably 3; L 1 and L 2 are chemical linkers; M 1 and M 2 are pharmacologically and/or biologically active moieties; and the bond between L 1 and M 1 and the bond between L 2 and M 2 are of the known chemical natures, including covalent and ionic. Compared with other previously described carrier peptides, this new family presents several advantages including its non-viral origin, its amphipathic character, its solubility in water and the absence of a cytotoxic effect at high concentrations. M 1 -L 1 -(Val-Arg-Leu-Pro-Pro-Pro) x -L 2 -M 2 (I)