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              Click Peptide多肽合成服务

              疏水性多肽不仅制备过程非常耗时而且即使在成功合成后由于其难溶等特性也很可能导致在筛选等实验操作时再次遇到障碍严重影响实验的进程。典型的疏水肽如β-amyloid它是阿尔茨海默病(Alzheimer's disease)治疗研究的有效靶点之一但由于其不可调控及易聚集的特性使研究进程常常无法顺利进行。金斯瑞专业的"Click Peptide"多肽合成服务(SC1497)可帮助客户有效解决疏水性肽的难溶及聚集问题。

              • 服务特色
              • 原理
              • 示例

              关键特征

              1. 改变疏水性肽的特征:
              • 物理化学性质(如:水溶性聚集自组装或折叠)
              • 生物学活性(如:配体-受体亲和力或酶-底物亲和力)
              2. 简单操作即可实现转变:
              • 合成的"click peptide"在pH值等于或高于7.4的条件下能轻易转变成您需要的疏水性多肽
              • 单向转化反应过程迅速
              • 转化过程无副产物,适用于生物学实验

              主要优势

              • 有效增加疏水性多肽的溶解度满足您的实验需求
              • 显著降低疏水性肽的聚集反应
              • 为AD实验中研究β-amyloid (1-42)的生物学功能研究提供了新的方法
              • 适用于细胞信号转导及其它研究

              参考文献

              • Atsuhiko Taniguchi, Youhei Sohma, et al. Click peptide: Chemical Biology-oriented analogues of Alzheimer's amyloid β peptide 1–42. J. Peptide Science. Nov 2006; 12(12): 823-828

              • Youhei Sohma, Atsuhiko Taniguchi, et al. Controlled Production of Amyloid β Peptide from a Photo-Triggered, Water-Soluble Precursor "Click Peptide". ChemBioChem. Nov 2008; 9(18): 3055-3065

              • Hui Wang, Taeko Kakizawa, et al. Synthesis of amyloid β peptide 1–42 (E22Δ) click peptide: pH-triggered in situ production of its native form. Bioorganic & Medicinal Chemistry. July 2009; 17(14): 4881-4887

              "click peptide"是指化学修饰后的多肽前体它常常被用于研究多肽的生物学功能。我们在目的多肽的骨架上进行了化学修饰构建多肽前体且该前体不具备目的肽固有的生物学活性当您收到多肽产品后只需通过简单的操作如改变pH值就能将前体肽原位转化为目的多肽无副产物产生。该反应速度快操作简单且转化过程不可逆。

              我们的click peptide服务参考了Atsuhiko Taniguchi等科学家研发的O-酰基肽方法(O-acyl isopeptide method图一)。多肽链间的氢键作用力可维持高级结构的构象稳定从而在物理化学性质及生物学功能中起着至关重要的作用。在pH值为7.4或更高的条件下前体肽链中发生原子经济性反应(atom-economical reaction)通过O→N分子内酰基转移迅速形成酰胺键。由于前体肽在转化过程中无副产品释放因此在毒理学研究试验中将占很大的优势。


              click peptide的转化反应

              参考文献

              Atsuhiko Taniguchi, Youhei Sohma, et al. Click peptide: Chemical Biology-oriented analogues of Alzheimer's amyloid β peptide 1–42. J. Peptide Science. Nov 2006; 12(12): 823-828

              26-O-acyl β-amyloid (1-42) click peptide was successfully synthesized, the β-ester bond in which can be quickly and quantitatively converted to a native Gly25-Ser26 amide bond via a pH-dependent O-N intramolecular acyl migration reaction (t1/2 =1 min, pH 7.4, 37℃) at a hydroxyamino acid residue. Namely, upon this pH-triggered conversion (pH-click), the non-aggregative and water-soluble precursor (click peptide) can produce the monomer with a random-coil structure under physiological conditions (pH 7.4, 37℃). The structure information is as follows.

              Scheme 2: β-amyloid (1-42) click peptide Result


              Result

              • β-amyloid precursor(click peptide) has a water solubility of 15 mg/ml, while it is only 0.14 mg/ml for the native peptide.
              • The aggregative property of the peptides reduced significantly.
              • The O-acyl moiety was stable under acidic pH.

              The following are HPLC reports of (Scheme 3) purified β-amyloid (1-42) native peptide converted from β-amyloid (1-42) click peptide (precursor) and (Scheme 4) purified 26-O-acyl β-amyloid (1-42) click peptide (precursor).


              Scheme 3: HPLC report of purified β-amyloid (1-42) native peptide converted from β-amyloid (1-42) click peptide (precursor)


              Scheme 4: HPLC report of purified 26-O-acyl β-amyloid (1-42) click peptide (precursor)

              订购信息

              Order by mail 邮箱: peptide@genscript.com.cn
              Order by phone 电话: 400-025-8686-5811