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Practical N-to-C peptide synthesis with minimal protecting groups
Toshifumi Tatsumi1, Koki Sasamoto1, Takuya Matsumoto1
1Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo, 113-0033, Japan.
Communications Chemistry
|October 26, 2023
Summary
This study introduces a new, eco-friendly peptide synthesis method. It uses an N-to-C strategy with unprotected amino acids, reducing chemical waste and enabling efficient peptide production.
Area of Science:
- Chemical Synthesis
- Organic Chemistry
- Biomaterials Science
Background:
- Peptides are crucial in pharmaceuticals and biomaterials.
- Traditional C-to-N peptide synthesis generates significant chemical waste.
- Environmental concerns necessitate greener synthesis approaches.
Purpose of the Study:
- To develop an environmentally friendly peptide synthesis method.
- To explore an alternative N-to-C elongation strategy.
- To reduce waste and improve atom efficiency in peptide production.
Main Methods:
- Catalytic peptide thioacid formation.
- Oxidative peptide bond formation under aerobic conditions.
- Utilizing main chain-unprotected amino acids.
- Employing a recyclable N-hydroxy pyridone additive to prevent epimerization.
Main Results:
- Successful application of the N-to-C strategy for iterative and fragment couplings.
- Elimination of the need for elaborate condensation reagents and protecting groups.
- Demonstrated practical synthesis of the nonapeptide DSIP.
- Suppression of epimerization during synthesis.
Conclusions:
- The novel N-to-C peptide synthesis is clean and atom-efficient.
- This method offers a sustainable alternative to traditional peptide synthesis.
- It facilitates the production of peptides with reduced environmental impact.
