Recent Progress on Green Methods and Technologies for Efficient Formation of Amide Bonds

doi:10.6023/cjoc202309011

Abstract

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

Cite this article

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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Fig. & Tab. 17

Scheme 1. Methods for amide synthesis

Figure 1. Common boron-based catalyst for direct amidation

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

Scheme 2. Typical enzyme-catalyzed amidation reaction

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

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

Figure 5. Examples of peptides synthesized in green solvents

Figure 6. Common new green solvents for peptide synthesis

Scheme 3. Representative acylation reaction in green solvent

Figure 7. Examples of peptides synthesized in cyrene

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

Figure 9. Structure of couping reagent

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

Scheme 5. Schematic diagram of physically enhanced peptide synthesis technology

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

Figure 11. Synthesis of peptides via micro-flow reaction

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

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