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ZHAO Yue, ZHAO Haibo, LENG Xiaojing, ZHAO Xiaoning, WANG Bingyue. Progress in Peptide Chemical Synthesis and its Metrology[J]. Metrology Science and Technology. doi: 10.12338/j.issn.2096-9015.2024.0215
Citation: ZHAO Yue, ZHAO Haibo, LENG Xiaojing, ZHAO Xiaoning, WANG Bingyue. Progress in Peptide Chemical Synthesis and its Metrology[J]. Metrology Science and Technology. doi: 10.12338/j.issn.2096-9015.2024.0215

Progress in Peptide Chemical Synthesis and its Metrology

doi: 10.12338/j.issn.2096-9015.2024.0215
  • Received Date: 2024-06-30
  • Accepted Date: 2024-07-09
  • Rev Recd Date: 2024-07-31
  • Available Online: 2024-09-05
  • Peptides are an important class of organic molecules in life bodies, and they participate in life activities together with proteins. Peptides, which have strong biological activity and biological functions, have been widely used in new materials, biological medicine, food, cosmetics and other fields. And they have tremendous social and economic value. In recent years, the rapid development of peptide synthesis technology, especially the rapid development of peptide chemical synthesis method, has greatly accelerated the development and application of peptide products. In the face of more and more peptide products on the market, the market demand for biological activity analysis of peptide compounds is increasing. And at the same time, the standardization of quality control of peptide products is also put forward. As a science of measurement, metrology technology can ensure that the measurement results can be reproduced and traced, and plays a critical role in the development and production of peptides and the quality control of related products. Developing peptide/protein metrology, which focuses on the research to achieve the accuracy and consistency of biological measurement and to ensure the measurement results can be traced to the international system of Units (SI), is an urgent and arduous task for metrology workers. This paper comprehensively introduces the chemical synthesis strategies of peptides, along with the advantages and disadvantages of these strategies, and application values. Meanwhile, the development, application and challenges of peptide/protein metrology are also introduced. This article intends to provide a reference for the quality control of peptide/protein products.
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  • [1]
    杨晓男, 阮丽君, 江兴, 等. 多肽类药物与中药肽研究展望[J]. 中国中药杂志, 2022, 47(22): 5978-5990.
    [2]
    KHEZRIAN A, AHMADI M, MOKARRAM P, et al. A Review of Recent Advances in Peptide-Based Anticancer Therapeutic Vaccines and Nanovaccines in Prostate Cancer[J]. International Journal of Peptide Research and Therapeutics, 2023, 29(5): 70. doi: 10.1007/s10989-023-10542-1
    [3]
    ZAHEDIPOUR F, JAMIALAHMADI K, ZAMANI P, et al. Improving the efficacy of peptide vaccines in cancer immunotherapy[J]. International Immunopharmacology, 2023, 123: 110721. doi: 10.1016/j.intimp.2023.110721
    [4]
    LIU L, BUSUTTIL K, ZHANG S, et al. The role of self-assembling polypeptides in building nanomaterials[J]. Physical Chemistry Chemical Physics, 2011, 13(39): 17435-17444. doi: 10.1039/c1cp21338e
    [5]
    FOSGERAU K, HOFFMANN T. Peptide therapeutics: current status and future directions[J]. Drug Discovery Today, 2015, 20(1): 122-128. doi: 10.1016/j.drudis.2014.10.003
    [6]
    MUTTENTHALER M, KING G F, ADAMS D J, et al. Trends in peptide drug discovery[J]. Nature Reviews Drug Discovery, 2021, 20(4): 309-325. doi: 10.1038/s41573-020-00135-8
    [7]
    李晓杰, 李富强, 朱丽萍, 等. 生物活性肽的制备与鉴定进展[J]. 山东轻工业学院学报(自然科学版), 2021, 35(1): 23-28.
    [8]
    胡玉玺, 蒋煜, 韩天娇. 制备工艺和过程控制对合成多肽药物有关物质的影响[J]. 中国新药杂志, 2017, 26(18): 2143-2148.
    [9]
    YAN H, CHEN F E. Recent Progress in Solid‐Phase Total Synthesis of Naturally Occurring Small Peptides[J]. Advanced Synthesis & Catalysis, 2022, 364(12): 1934-1961.
    [10]
    JIMMIDI R. Synthesis and Applications of Peptides and Peptidomimetics in Drug Discovery[J]. European Journal of Organic Chemistry, 2023, 26(18): 24-40.
    [11]
    YANG S, WANG M, WANG T, et al. Self-assembled short peptides: Recent advances and strategies for potential pharmaceutical applications[J]. Materials Today Bio, 2023, 20: 100644. doi: 10.1016/j.mtbio.2023.100644
    [12]
    CHEN M, YU X. tert-Butyloxycarbonyl-protected amino acid ionic liquids and their application to dipeptide synthesis[J]. RSC Advances, 2021, 11(44): 27603-27606. doi: 10.1039/D1RA05597F
    [13]
    FUSE S , KOINUMA H , KIMBARA A, et al. Total synthesis and stereochemistry revision of mannopeptimycin aglycone [J]. Journal of the American Chemical Society, 2014, 136(34): 12011-12017.
    [14]
    刘豪, 刘冬梅, 孙浩田, 等. 利用脂溶性硅基载体连续流动液相合成维洛斯肽[J]. 高等学校化学学报, 2024, 45(7): 9-17.
    [15]
    王宏慧. 几种寡肽的固相合成及其与DNA的相互作用 [D]. 郑州: 河南工业大学, 2010.
    [16]
    HARINGTON C R, MEAD T H. Synthesis of glutathione[J]. Biochemical Journal, 1935, 29(7): 1602. doi: 10.1042/bj0291602
    [17]
    VIGNEAUD V D, RESSLER C, SWAN C J M, et al. The synthesis of an octapeptide with hormonal activity of oxytocin[J]. Journal of the American Chemical Society, 1953, 75(19): 328-332.
    [18]
    HATTORI K, KOIKE K, OKUDA K, et al. Solution-phase synthesis and biological evaluation of triostin A and its analogues[J]. Organic & Biomolecular Chemistry, 2016, 14(6): 2090-2111.
    [19]
    ZHANG T, SONG W, ZHAO J, et al. Full Solution-Phase Synthesis of Acetyl Hexapeptide-3 by Fragments Coupling Strategy[J]. Industrial & Engineering Chemistry Research, 2017, 56(41): 11697-11704.
    [20]
    李士杰, 杨洋, 崔营营, 等. 微通道连续流高效绿色合成亮丙瑞林[J]. 高等学校化学学报, 2020, 41(7): 1559-1566.
    [21]
    LIU X, ZHANG N, GU X, et al. Total synthesis of semaglutide based on a soluble hydrophobic-support-assisted liquid-phase synthetic method[J]. ACS Combinatorial Science, 2020, 22(12): 821-825. doi: 10.1021/acscombsci.0c00134
    [22]
    MASUI H, FUSE S. Recent Advances in the Solid- and Solution-Phase Synthesis of Peptides and Proteins Using Microflow Technology[J]. Organic process research & development, 2022, 26(6): 1751-1765.
    [23]
    郑龙, 田佳鑫, 张泽鹏, 等. 多肽药物制备工艺研究进展[J]. 化工学报, 2021, 72(7): 13. doi: 10.11949/0438-1157.20210270
    [24]
    MERRIFIELD R B. Merrifield Solid-Phase Peptide Synthesis (SPPS)[J]. Journal of the American Chemical Society, 1963, 85: 2149-2152. doi: 10.1021/ja00897a025
    [25]
    SATO R, Oyama K, Konno H. Investigation for the cyclization efficiency of linear tetrapeptides: Synthesis of tentoxin B and dihydrotentoxin[J]. Tetrahedron, 2018, 74(42): 6173-6181. doi: 10.1016/j.tet.2018.09.011
    [26]
    时华曜, 范崇旭, 代先东, 等. 微波辅助RGD环肽的固相合成[J]. 合成化学, 2019, 27(2): 137-140.
    [27]
    史文泽, 袁瑜, 黄波, 等. 瑞莫瑞林的Fmoc固相合成及其活性检测[J]. 中国药物化学杂志, 2022, 32(8): 613-618.
    [28]
    JENSEN K J. Solid-phase peptide synthesis: an introduction [M]. In: Jensen K J, Shelton T P, Pedersen S L. (eds) Peptide Synthesis and Applications. Methods in Molecular Biology. Humana Press, Totowa, NJ, 2013, 1047: 1-21.
    [29]
    黄蓓. 多肽固相合成研究进展[J]. 河南化工, 2013, 3(1): 28-58.
    [30]
    王新月, 金康. 多肽及蛋白质的化学合成研究[J]. 化学进展, 2023, 35(4): 526-542. doi: 10.7536/PC220930
    [31]
    吴一凡, 刘福利. 多肽固相合成中起始物料的控制策略[J]. 中国新药杂志, 2022, 31(10): 937-941. doi: 10.3969/j.issn.1003-3734.2022.10.003
    [32]
    朱玥. 反向固相多肽合成方法新策略及其应用 [D]. 衡阳: 南华大学, 2021.
    [33]
    董莲华, 刘亚辉, 傅博强, 等. 生物计量研究现状及展望[J]. 计量学报, 2023, 44(3): 317-325.
    [34]
    武利庆, 王晶. 蛋白质计量发展现状和趋势[J]. 中国计量, 2007(2): 21-22. doi: 10.3969/j.issn.1006-9364.2007.02.010
    [35]
    李明, 李红梅, 李孟婉. C肽的国际比对及C肽纯度标准物质的研制[J]. 计量技术, 2020(5): 112-114.
    [36]
    李明, 张伟. 基于有机元素分析的多肽纯度测量技术[J]. 计量科学与技术, 2022(7): 18-21.
    [37]
    王晶, 武利庆. 中国计量院生物计量之蛋白质计量研究进展[J]. 中国计量, 2016(7): 27-28.
    [38]
    霍中中, 冯流星, 李红梅, 等. 基于硫同位素稀释质谱法的β淀粉样多肽绝对定量研究[J]. 分析化学, 2019, 47(12): 1931-1937.
    [39]
    WANG S, WU P, LI M, et al. Mass balance method for SI-traceable purity assignment of synthetic oxytocin[J]. Journal of Pharmaceutical and Biomedical Analysis, 2022, 207: 114401. doi: 10.1016/j.jpba.2021.114401
    [40]
    全国生物计量技术委员会. 糖化血红蛋白分析仪校准规范: JJF 1841-2020 [S]. 北京: 国家市场监督管理总局, 2020.
    [41]
    全国生物计量技术委员会. C反应蛋白分析仪校准规范: JJF 2057-2023 [S]. 北京: 国家市场监督管理总局, 2023.
    [42]
    全国生物计量技术委员会. 全自动酶联免疫分析仪校准规范: JJF 2089-2023 [S]. 北京: 国家市场监督管理总局, 2023.
    [43]
    BRANGE J, LANKJOER L. Insulin structure and stability [M]. In: Wang Y J, Pearlman R. (eds) Stability and Characterization of Protein and Peptide Drugs. Pharmaceutical Biotechnology, Springer Press, Boston, MA, 1993, 5: 315-350.
    [44]
    张春阳, 张海洋. 血常规联合肿瘤标志物检测在直肠癌诊断中的应用价值分析[J]. 中国肛肠病杂志, 2022(1): 3-5. doi: 10.3969/j.issn.1000-1174.2022.01.002
    [45]
    JONES G R D. The role of EQA in harmonization in laboratory medicine – a global effort[J]. Biochemia Medica, 2017, 27(1): 23-29.
    [46]
    DORNER B G, RUMMEL A. Preface Biological Toxins—Ancient Molecules Posing a Current Threat[J]. Toxins, 2015, 7(12): 5320-5321. doi: 10.3390/toxins7124888
    [47]
    LIU W, BUTLER E, YANG H Y, et al. Informatics Approaches to Forensic Body Fluid Identification by Proteomic Mass Spectrometry [M]. Applications in Forensic Proteomics: Protein Identification and Profiling, American Chemical Society Press, Washington, DC, 2019, 81-90.
    [48]
    MEDVEDEVSKIKH M Y, SERGEEVA A S. Problems of Ensuring Metrological Traceability of Quality Control Measurement Results for Food Products and Food Raw Materials[J]. Measurement Techniques, 2020, 63(3): 242-248. doi: 10.1007/s11018-020-01777-1
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