Fmoc-Val-Ala-Ala-Leu-Lys(Boc)-Ser(ψMe,Mepro)-Lys(Boc)-OH | 1333407-42-3

• 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
• 英文名称: Fmoc-Val-Ala-Ala-Leu-Lys(Boc)-Ser(ψMe,Mepro)-Lys(Boc)-OH
• CAS: 1333407-42-3
• 化学式: C₆₀H₉₁N₉O₁₅
• 分子量: 1178.43
• InChiKey: KFZYBQDRKQZJIP-ZOMTYDRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  84.0
• 可旋转键数：
  28.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  327.33
• 氢给体数：
  9.0
• 氢受体数：
  14.0

反应信息

• 作为产物：
  描述：

  Fmoc-L-缬氨酸 、 Fmoc-L-亮氨酸 、 Fmoc-L-丙氨酸 、 Fmoc-Lys-(Boc)-Ser(ψMe,Mepro)-OH 、 N-alpha-芴甲氧羰基-N-epsilon-叔丁氧羰基-L-赖氨酸 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 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 Fmoc-Val-Ala-Ala-Leu-Lys(Boc)-Ser(ψMe,Mepro)-Lys(Boc)-OH
  参考文献：
  名称：

  Coiled Coil Peptides as Universal Linkers for the Attachment of Recombinant Proteins to Polymer Therapeutics

  摘要：

  We have designed, synthesized, and characterized peptides containing four repeats of the sequences VAALEKE (peptide E) or VAALKEK (peptide K). While the peptides alone adopt in aqueous solutions a random coil conformation, their equimolar mixture forms heterodimeric coiled coils as confirmed by CD spectroscopy. S-Azidopentanoic acid was connected to the N-terminus of peptide E via a short poly(ethylene glycol) spacer. The terminal azide group enabled conjugation of the peitide with a synthetic drug carrier based on the N-(2-hydrokypropyl)methacrylamide copolymer containing propargyl groups using "click" chemistry. When incorporated into the polymer drug carrier, peptide E formed a stable noncovalent complex with peptide K beloning to a recombinant single-chain fraginent (scFv) of the M75 antibody. The complex thereby mediates a noncovalent linkage between the polymer drug carrier and the protein. The recombinant scFv antibody fragment was selected as a targeting ligand against carbonic anhydrase IX-a marker overexpressed by tumor cells of various human carcinomas. The antigen binding affinity of the polymer-scFv complex was confirmed by ELISA. This approach offers a well-defined, specific, and nondestructive universal method for the preparation of protein (antibody)-targeted polymer drug and gene carriers designed for cell-specific delivery.

  DOI：

  10.1021/bm200897b