酰胺键的绿色高效构建方法与技术进展

doi:10.6023/cjoc202309011

摘要/Abstract

在多肽合成与药物化学研究中, 酰胺键形成反应是至关重要的. 传统的酰胺键构建方法要使用过量试剂和大量溶剂, 对环境和人类健康构成严重威胁, 因而开发环境友好的新颖酰化试剂、高效绿色可持续的酰胺键合成方法, 以实现酰胺的选择性合成仍然是当前的研究热点. 在绿色化学的背景下, 重点介绍了近几年绿色高效构建酰胺键的方法, 包括元素有机物催化、绿色溶剂和绿色试剂的发展以及应用物理强化技术等, 特别强调了这些方法在多肽合成中的应用.

关键词: 酰胺键, 催化, 绿色化学, 多肽

Amide bond constructions are crucial in peptide synthesis and pharmaceutical chemistry research. The traditional methods of peptide synthesis require the use of excessive amounts reagents and solvents, posing a threat to the environment and human health. It is still the current research focus to develop environmentally friendly novel acylation reagents and efficient, green, and sustainable amide bond synthesis methods. From the green chemistry’s principles, this paper is focused on the efficient formation of amide bonds in peptide, including the catalysis of elemental organic chemicals, some green solvents and reagents, and some physical strengthening methods, etc. The application of these methods and technologies was also discussed in peptide chemistry.

Key words: amidation, catalysis, green chemistry, peptide

引用此文

黄净, 杨毅华, 张占辉, 刘守信. 酰胺键的绿色高效构建方法与技术进展[J]. 有机化学, 2024, 44(2): 409-420.

Jing Huang, Yihua Yang, Zhanhui Zhang, Shouxin Liu. Recent Progress on Green Methods and Technologies for Efficient Formation of Amide Bonds[J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 409-420.

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图/表 17

图式1. 酰胺键构建方法

Scheme 1. Methods for amide synthesis

图1. 常见直接酰胺化的硼化合物催化剂

Figure 1. Common boron-based catalyst for direct amidation

图2. 硼或锆化合物催化构建的酰胺化合物的例证

Figure 2. Examples of amide compounds catalyzed by boron or zirconium compounds

图式2. 典型酶催化酰胺化反应

Scheme 2. Typical enzyme-catalyzed amidation reaction

图3. 不同酶催化合成酰胺键的化合物(部分)

Figure 3. Efficient green catalytic synthesis of amide bonds by different enzymes

图4. 多肽合成中水溶性N-保护基

Figure 4. Water-soluble sulfone-derived amino acid protecting groups

图5. 绿色溶剂中合成的肽类化合物示例

Figure 5. Examples of peptides synthesized in green solvents

图6. 常见的几种多肽合成的新绿色溶剂

Figure 6. Common new green solvents for peptide synthesis

图式3. 绿色溶剂中代表性酰化反应

Scheme 3. Representative acylation reaction in green solvent

图7. 二氢左旋葡萄糖酮中合成的肽类化合物示例

Figure 7. Examples of peptides synthesized in cyrene

图8. SPPS中可替代哌啶脱除Fmoc-的有机碱

Figure 8. Organic bases replaced piperidine for Fmoc-removal in SPPS

图9. 缩合剂的结构

Figure 9. Structure of couping reagent

图式4. T3P缩合剂反应过程和H-Tyr-Ile-Gly-Phe-Leu-NH2

Scheme 4. T3P reaction process of T3P? and structure of H- Tyr-Ile-Gly-Phe-Leu-NH2

图式5. 物理强化多肽合成技术示意图

Scheme 5. Schematic diagram of physically enhanced peptide synthesis technology

图10. Aspartame 和VVIA四肽的结构式以及三种方法合成四肽VVIA的产率和纯度比较

Figure 10. Structural formula of aspartame and VVIA, and yields and purities for the three strategies of tetrapeptide VVIA synthesis

图11. 微流技术合成的肽示例

Figure 11. Synthesis of peptides via micro-flow reaction

图式6. 可见光辅助能合成二肽和三肽

Scheme 6. Synthesis of dipeptides and tripeptides assisted by visible light

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