One-pot and sustainable liquid-phase peptide extension for synthesis of C-terminal amidation peptides aided by small molecular tags

Li, Haidi; Jin, Yuankui; Wang, Lianjun; Zhang, Linyan; Liu, Tianyu; Liu, Yu; Liang, Taigang

doi:10.1039/d3qo01248d

Org. Chem. Front.

2023

DOI: 10.1039/d3qo01248d

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One-pot and sustainable liquid-phase peptide extension for synthesis of C-terminal amidation peptides aided by small molecular tags

Haidi Li,

Yuankui Jin,

Lianjun Wang

et al.

Abstract: The development of greener and more economical methods for peptide synthesis has been a driving force in promoting the large-scale production of peptide drugs. In this study, we present a...

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2024

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Cited by 2 publications

References 26 publications

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TAG‐Assisted Liquid‐Phase Synthesis and Structure Activity Relationship of Macolacin‐Based Side‐to‐Tail Cyclopeptides Antibiotic

Li,

Jin,

Pei

et al. 2024

Chin. J. Chem.

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Comprehensive SummaryTAG‐assisted peptide synthesis technology enables optimal conservation of Fmoc amino acid raw materials and chemical solvents while eliminating the need for intricate chromatographic purification processes. This work presents a 4,4'‐diphenylphosphonoxy diphenylcarbinol tag‐mediated liquid‐phase synthesis approach for preparing side‐to‐tail cyclopeptides macolacin which has strong activity against gram‐negative bacteria, and its 15 analogues containing four N‐methylation modified cyclopeptides, as well as an investigation of their structure‐activity relationship (SAR). The synthesis of macolacin analogues primarily focuses on the modifications of the N‐methylation group of Ile‐7 and the tail fatty acyl chain of macolacin. The incorporation of N‐methylation for Ile‐7, along with the dihalogenated or monohalogenated benzoic acids for tail modification, exhibited remarkable antibacterial efficacy and minimal hepatocellular toxicity in vitro. The present study identified an N‐methylation‐modified antimicrobial cyclopeptide Ma14 that exhibits rapid bactericidal efficacy against A. baumanii, etc., while showing reduced hepatocellular toxicity. Molecular docking simulations were conducted to investigate the binding of cyclopeptides to the outer membrane protein BamA of A. baumannii. The findings demonstrated the stable binding interactions of the cyclopeptides with the BamA protein and then presented a novel approach to explain the bacteriostatic mechanism of macolacin‐based cyclopeptide antibiotics.

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TAG‐Assisted Liquid‐Phase Synthesis and Structure Activity Relationship of Macolacin‐Based Side‐to‐Tail Cyclopeptides Antibiotic

Li,

Jin,

Pei

et al. 2024

Chin. J. Chem.

View full text Add to dashboard Cite

show abstract

Scalable preparation of green C-terminal amidation peptide-synthesis TAGs and the optimized TAG-assisted liquid-phase synthesis of eptifibatide

Li,

Wang,

Zhang

et al. 2024

Sustainable Chemistry and Pharmacy

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One-pot and sustainable liquid-phase peptide extension for synthesis of C-terminal amidation peptides aided by small molecular tags

Abstract: The development of greener and more economical methods for peptide synthesis has been a driving force in promoting the large-scale production of peptide drugs. In this study, we present a...

Cited by 2 publications

References 26 publications

TAG‐Assisted Liquid‐Phase Synthesis and Structure Activity Relationship of Macolacin‐Based Side‐to‐Tail Cyclopeptides Antibiotic

TAG‐Assisted Liquid‐Phase Synthesis and Structure Activity Relationship of Macolacin‐Based Side‐to‐Tail Cyclopeptides Antibiotic

Scalable preparation of green C-terminal amidation peptide-synthesis TAGs and the optimized TAG-assisted liquid-phase synthesis of eptifibatide

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