Synthesis of a Phosphorylated Polypeptide by a Thioester Method
Synthesis of a Phosphorylated Polypeptide by a Thioester Method
复制标题
硫酯法合成磷酸化多肽
DOI：
10.1007/0-306-46880-8_46
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发表时间：
2000
影响因子：
4
通讯作者：
S. Aimoto
中科院分区：
文献类型：
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作者：
T. Kawakami;K. Hasegawa;S. Aimoto
通过合成磷酸化cAMP反应元件结合蛋白1(19-106)酰胺[Thr(PO3H2)69,71]-CRE BP1(19-106)-NH2作为模型化合物，研究了磷酸化多肽的合成方法。三个部分保护的肽片段：Boc-[Lys(Boc)23,46,48,54, Cys(Acm)27,32]-CRE BP1(19-56)-SCH2CH2CO-β-Ala-NH2, Fmoc-[Thr(PO3H2)69,71, Lys(Boc)77, Cys(Acm)79]-CRE BP1(57-83)-SCH2CH2CO-β-Ala-NH2 和 [Lys(Boc)97,98,105,106]-CRE BP1(84-106)-NH2 通过 Boc 固相法制备并用作结构单元。在银化合物、HOObt和DIEA存在下通过硫酯法依次进行链段缩合。去除肽上的所有保护基团后，基于 C 端结构单元，以 19% 的产率获得了所需的产物。这些结果表明硫酯法对于磷酸化多肽的制备非常有用，即使它含有半胱氨酸残基。仍有待改进的一件事是用于制备含有磷酸化氨基酸残基的部分保护的肽硫酯的方法的效率。
A method for the synthesis of phosphorylated polypeptides was investigated through the synthesis of the phosphorylated cAMP response element binding protein 1 (19-106) amide, [Thr(PO3H2)69,71]-CRE BP1(19-106)-NH2, as a model compound. Three partially protected peptide segments: Boc-[Lys(Boc)23,46,48,54, Cys(Acm)27,32]-CRE BP1(19-56)-SCH2CH2CO-β-Ala-NH2, Fmoc-[Thr(PO3H2)69,71, Lys(Boc)77, Cys(Acm)79]-CRE BP1(57-83)-SCH2CH2CO-β-Ala-NH2, and [Lys(Boc)97,98,105,106]-CRE BP1(84-106)-NH2, were prepared by the Boc solid-phase method and were used as building blocks. The segment condensations were carried out sequentially by a thioester method in the presence of a silver compound, HOObt, and DIEA. The desired product was obtained in 19% yield, based on the C-terminal building block, after removal of all the protecting groups on the peptide. These results indicate that the thioester method is quite useful for the preparation of phosphorylated polypeptide even if it contains cysteine residues. One thing which remains to be improved is the efficiency of the method for the preparation of partially protected peptide thioesters, which contain phosphorylated amino acid residues.
H.Hojo：“含 S-保护的半胱氨酸肽硫酯的制备及其在酿酒酵母 DNA 指导的 RNA 聚合酶 II 中合成 Barnase 样结构域的用途”Bull.Chem.Soc.Jpn.68。
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