4-Iodine N -Methylpyridinium-Mediated Peptide Synthesis

Through systematic optimization of halopyridinium compounds, we established a peptide coupling protocol utilizing 4-iodine -methylpyridinium ( ) for solid-phase peptide synthesis (SPPS). The coupling reagent is easily prepared, bench stable, and cost-effective. Employing in the SPPS process has show...

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Bibliographic Details
Published in:Organic letters 2023-12, Vol.25 (48), p.8661-8665
Main Authors: Zhong, Wanjin, Wan, Chuan, Zhou, Ziyuan, Dai, Chuan, Zhang, Yichi, Lu, Fei, Yin, Feng, Li, Zigang
Format: Article
Language:English
Subjects:
Amino Acids - chemistry
Peptides - chemistry
Pyridinium Compounds
Solid-Phase Synthesis Techniques - methods
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Summary:Through systematic optimization of halopyridinium compounds, we established a peptide coupling protocol utilizing 4-iodine -methylpyridinium ( ) for solid-phase peptide synthesis (SPPS). The coupling reagent is easily prepared, bench stable, and cost-effective. Employing in the SPPS process has showcased remarkable chemoselectivity and efficiency, effectively eliminating racemization and epimerization. This achievement has been substantiated through the successful synthesis of a range of peptides via the direct utilization of commercially available amino acid substrates for SPPS.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c03539