电化学修饰氨基酸和多肽类化合物的研究进展

doi:10.6023/cjoc202310024

摘要/Abstract

随着多肽类化合物在治疗肿瘤疾病和生物医学应用中重要性的与日俱增, 开发和构建多肽分子的新方法已成为有机合成化学家的研究热点. 近年来有机电化学作为一种绿色高效的反应工具, 被逐步运用于有机小分子合成领域, 其温和可控的特征适合解决现有生物偶联策略存在的化学和区域选择性问题, 为多肽分子的选择性修饰提供了一种重要的合成手段. 综述了近五年来利用电化学手段修饰氨基酸和多肽类化合物的反应, 阐述了电化学合成技术的优势及其在开发新型生物相容性方法中的适用性.

关键词: 有机电化学, 氨基酸, 多肽修饰, 化学和区域选择性

With the increasing importance of peptides in the treatment of oncological diseases and biomedical applications, the development and construction of new methods for peptide molecules have become a hot research topic for organic synthetic chemists. As a green and efficient reaction tool, organic electrochemistry has been gradually utilized in the field of organic small molecule synthesis in recent years, and its mild and controllable features are suitable for solving the chemo- and regioselectivity problems of the existing bioconjugation strategies, which provide an important synthetic means for the selective modification of peptide molecules. The electrochemical approaches to amino acids and peptides modification developed in the last five years are reviewed, and the distinct advantages of electrochemical synthesis techniques and its applicability in the development of novel biocompatible methodologies are described.

Key words: organic electrochemistry, amino acids, peptide modifications, chemo- and regio-selectivity

引用此文

方新月, 黄雅雯, 胡新伟, 阮志雄. 电化学修饰氨基酸和多肽类化合物的研究进展[J]. 有机化学, 2024, 44(3): 903-926.

Xinyue Fang, Yawen Huang, Xinwei Hu, Zhixiong Ruan. Recent Progress in Electrochemical Modification of Amino Acids and Peptides[J]. Chinese Journal of Organic Chemistry, 2024, 44(3): 903-926.

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图/表 31

图1. 代表性的多肽类药物

Figure 1. Representative peptide drugs

图2. 基于小分子试剂的电化学活化实现多肽和蛋白质的酪氨酸修饰

Figure 2. Tyrosine modification of peptides and proteins by electrochemical activation of small-molecule reagents (A) e-Y-click reaction, (B) modified e-Y-click reaction, (C) modification of Trastuzumab

图3. 电化学活化吩噻嗪衍生物实现多肽和蛋白质的酪氨酸修饰

Figure 3. Tyrosine modification of peptides and proteins by electrochemical activation of phenothiazine derivatives

图4. 铑-电催化2-羟基苯甲醛酪氨酸类似物与炔烃的环化反应

Figure 4. Rhodium-electrocatalyzed cyclization of 2-hydroxybenzaldehyde tyrosine analogues with alkynes

图5. 钌-电催化C—H酰氧基化实现多肽的酪氨酸修饰

Figure 5. Tyrosine modification of peptides by ruthenium-electrocatalyzed C—H acylation

图6. 电化学介导酪氨酸与邻氨基苯甲酸衍生物的反应及机理

Figure 6. Electrochemically mediated reaction and mechanism of tyrosine with o-aminobenzoic acid derivatives

图7. 电化学促进多肽和蛋白质的色氨酸选择性生物偶联

Figure 7. Electrochemically-promoted tryptophan-selective bioconjugation of peptides and proteins

图8. 电化学介导色氨酸衍生物的卤代环化反应

Figure 8. Electrochemically mediated halogenation cyclization reaction of tryptophan derivatives

图9. (A)锰-电催化叠氮化/杂环化串联实现多肽的色氨酸修饰、(B)立体构型和(C)可能的反应机理

Figure 9. (A) Tryptophan modification of peptides by manganese-electrocatalyzed azide/heterocyclization cascades, (B) stereo configuration, and (C) proposed mechanism

图10. (A)电光催化色氨酸的三氟甲基化反应和(B)电化学介导色氨酸的三氟甲基化反应及机理

Figure 10. (A) Electrophotocatalyzed trifluoromethylation of tryptophan, and (B) electrochemically mediated trifluoromethylation and mechanism of tryptophan

图11. -1 镍-电催化对溴苯丙氨酸与胺的C—N交叉偶联反应

Figure 11. -1 Nickel-electrocatalyzed C—N cross-coupling reaction of p-bromophenylalanine with amines

图11. -2 镍-电催化对溴苯丙氨酸与胺的C—N交叉偶联反应的机理

Figure 11. -2 Mechanism of C—N cross-coupling reaction between p-bromophenylalanine and amines by nickel-electrocatalyzed

图12. 电化学介导脯氨酸的α-甲基化反应

Figure 12. Electrochemically mediated α-methylation of proline

图13. 电化学介导半胱氨酸的脱硫反应及机理

Figure 13. Electrochemically mediated desulfurization and mechanism of cysteine

图14. 硒代半胱氨酸的电化学硒醚化反应及机理

Figure 14. Electrochemical selenoetherification and mechanism of selenocysteine

图15. 电化学介导丝氨酸的级联环化反应及机理

Figure 15. Electrochemically mediated cascade annulation and mechanism of serine

图16. 甘氨酸的电化学修饰

Figure 16. Electrochemical modification of glycine (A) Electrochemically mediated intramolecular oxidative cyclization of glycine derivatives, and (B) electrochemically mediated phosphorylation and mechanism of glycine derivatives

图17. 电化学介导多肽N末端邻苯二甲酰亚胺的还原反应

Figure 17. Electrochemically mediated reduction of N-terminal phthalimides of peptides

图18. 硒-电催化2-乙烯基芳胺的脱氢环化反应

Figure 18. Selenium-electrocatalyzed dehydrocyclization of 2-vinylaromatic amines

图19. (A)铱-电催化烯烃与苯甲酸的环化反应、(B) N-芳基环胺的电化学去饱和β酰化反应、(C)电化学介导烷基卤化物的还原氘化反应和(D)电化学介导芳基环氧化物与二氧化碳的反应及机理

Figure 19. (A) Iridium-electrocatalyzed cyclization of olefins with benzoic acid, (B) electrochemical desaturative β-acylation of cyclic N-aryl amines, (C) electrochemically mediated reductive deuteration of alkyl halides, and (D) electrochemically mediated reaction and mechanism of aryl epoxides and carbon dioxide

图20. 金-电催化炔烃与芳基肼的C(sp)—C(sp2)偶联反应及机理

Figure 20. Gold-electrocatalyzed C(sp)—C(sp2) coupling reaction and mechanism of alkynes with arylhydrazines

图21. (A)电光催化芳烃的羟基化反应和(B)电光催化烯烃的乙酰氧基羟化反应

Figure 21. (A) Electrophotocatalytic hydroxylation of aromatic hydrocarbons, and (B) electrophotocatalytic acetoxyhydroxylation of olefins

图22. 电化学介导α-氨基酸的C(sp3)—N脱羧偶联反应

Figure 22. Electrochemically mediated C(sp3)—N decarboxylation coupling reaction of α-amino acids

图23. 电化学介导七肽的分子内脱羧环化反应

Figure 23. Electrochemically mediated intramolecular decarboxylative cyclization of heptapeptide

图24. 电化学介导氨基酸的脱羧乙酰氧基化反应

Figure 24. Electrochemically mediated decarboxylative acetoxylation of amino acids

图25. 电化学介导多肽的脱羧后期功能化修饰

Figure 25. Electrochemically mediated decarboxylation of peptides for late-stage functionalization

图26. 甘氨酸的电化学脱羧反应

Figure 26. Electrochemical decarboxylation of glycine (A) Electrochemically mediated decarboxylation cross-coupling reaction of N-substituted glycines, (B) electrochemically mediated cyclization reaction and mechanism of N-arylglycine with quinoxalin-2(1H)-ones, and (C) electrochemically mediated three-component reaction of N-arylglycine, N-sulfonyl- ketimine and formaldehyde

图27. 电化学介导氨基酸的α-甲氧基化反应

Figure 27. Electrochemically mediated α-methoxylation of amino acids

图28. 电化学介导氨基酸C末端羧基的酯化反应及机理

Figure 28. Electrochemically mediated esterification reaction and mechanism of C-terminal carboxyl group of amino acids

图29. 电化学介导氨基酸与硫化物的交叉偶联反应及机理

Figure 29. Electrochemically mediated cross-coupling reaction and mechanism of amino acids with sulfides

图30. (A)电化学介导的多肽合成、(B)亮丙瑞林的合成和(C)可能的机理

Figure 30. (A) Electrochemically mediated peptide synthesis, (B) synthesis of leuprolide, and (C) proposed mechanism

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