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Total synthesis of bovine pancreatic trypsin inhibitor and the protein diastereomer [Gly37D‐Ala]BPTI using Boc chemistry solid phase peptide synthesis
Peptide Science ( IF 1.5 ) Pub Date : 2020-04-11 , DOI: 10.1002/pep2.24166 Alexander J. Donovan 1 , Joanna Dowle 1 , Yanwu Yang 2 , Michael A. Weiss 2 , Stephen B. H. Kent 1
Peptide Science ( IF 1.5 ) Pub Date : 2020-04-11 , DOI: 10.1002/pep2.24166 Alexander J. Donovan 1 , Joanna Dowle 1 , Yanwu Yang 2 , Michael A. Weiss 2 , Stephen B. H. Kent 1
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Bovine pancreatic trypsin inhibitor (BPTI) is a well‐studied model for investigation of protein folding and stability. Here, we report the synthesis and characterization of wild‐type BPTI and a diastereomeric protein analogue [Gly37D‐Ala]BPTI. Each 58‐residue polypeptide chain was made by native chemical ligation of two peptide segments, BPTI[1‐29]‐αthioester and the appropriate version of the Cys30‐58 BPTI peptide segment. Boc chemistry in situ neutralization solid phase synthesis was used to prepare the peptide segment reactants. The resulting full‐length polypeptide chains were folded in a cysteine/cystine redox buffer to give synthetic protein molecules containing three disulfide bonds. The diastereomeric analogue [Gly37D‐Ala]BPTI folded as efficiently as the native protein. Synthetic proteins were characterized by analytical LCMS and by natural‐abundance 1H‐15N HSQC NMR fingerprinting. These results illustrate the power of Boc chemistry peptide synthesis and its utility for the total chemical synthesis of protein molecules.
中文翻译：
Boc化学固相肽合成法全合成牛胰胰蛋白酶抑制剂和蛋白质非对映异构体[Gly37D-Ala] BPTI
牛胰胰蛋白酶抑制剂（BPTI）是研究蛋白质折叠和稳定性的良好模型。在这里，我们报告了野生型BPTI和非对映体蛋白类似物[Gly37D-Ala] BPTI的合成和表征。每个58个残基的多肽链都是通过两个肽段BPTI [1-29] -α硫酯和适当版本的Cys 30的天然化学连接而制成的‐58 BPTI肽段。Boc化学原位中和固相合成用于制备肽段反应物。将得到的全长多肽链在半胱氨酸/胱氨酸氧化还原缓冲液中折叠，得到包含三个二硫键的合成蛋白分子。非对映异构体[Gly37D-Ala] BPTI的折叠效率与天然蛋白质一样。合成蛋白的特征在于分析型LCMS和自然丰度1 H - 15 N HSQC NMR指纹图谱。这些结果说明了Boc化学肽合成的力量及其在蛋白质分子总化学合成中的效用。
更新日期：2020-04-11
中文翻译：
Boc化学固相肽合成法全合成牛胰胰蛋白酶抑制剂和蛋白质非对映异构体[Gly37D-Ala] BPTI
牛胰胰蛋白酶抑制剂（BPTI）是研究蛋白质折叠和稳定性的良好模型。在这里，我们报告了野生型BPTI和非对映体蛋白类似物[Gly37D-Ala] BPTI的合成和表征。每个58个残基的多肽链都是通过两个肽段BPTI [1-29] -α硫酯和适当版本的Cys 30的天然化学连接而制成的‐58 BPTI肽段。Boc化学原位中和固相合成用于制备肽段反应物。将得到的全长多肽链在半胱氨酸/胱氨酸氧化还原缓冲液中折叠，得到包含三个二硫键的合成蛋白分子。非对映异构体[Gly37D-Ala] BPTI的折叠效率与天然蛋白质一样。合成蛋白的特征在于分析型LCMS和自然丰度1 H - 15 N HSQC NMR指纹图谱。这些结果说明了Boc化学肽合成的力量及其在蛋白质分子总化学合成中的效用。
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