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Open AccessArticle

Synthesis of Fmoc-Triazine Amino Acids and Its Application in the Synthesis of Short Antibacterial Peptidomimetics

1
Division of Magnetic Resonance, Korea Basic Science Institute (KBSI), Ochang 28119, Korea
2
Department of Medical Science, Graduate School, Chosun University, Gwangju 61452, Korea
3
Department of Bio-analytical Science, University of Science & Technology, Daejeon 34113, Korea
4
Department of Cellular and Molecular Medicine, School of Medicine, Chosun University, Gwangju 61452, Korea
*
Author to whom correspondence should be addressed.
These authors contributed equally to this work.
Int. J. Mol. Sci. 2020, 21(10), 3602; https://doi.org/10.3390/ijms21103602
Received: 22 April 2020 / Revised: 18 May 2020 / Accepted: 18 May 2020 / Published: 20 May 2020
To combat the escalating rise of antibacterial resistance, the development of antimicrobial peptides (AMPs) with a unique mode of action is considered an attractive strategy. However, proteolytic degradation of AMPs remains the greatest challenge in their transformation into therapeutics. Herein, we synthesized Fmoc-triazine amino acids that differ from each other by anchoring either cationic or hydrophobic residues. These unnatural amino acids were adopted for solid-phase peptide synthesis (SPPS) to synthesize a series of amphipathic antimicrobial peptidomimetics. From the antimicrobial screening, we found that the trimer, BJK-4 is the most potent short antimicrobial peptidomimetic without showing hemolytic activity and it displayed enhanced proteolytic stability. Moreover, the mechanism of action to kill bacteria was found to be an intracellular targeting. View Full-Text
Keywords: Fmoc-triazine-amino acids; antibacterials; short peptidomimetics; intracellular targeting; unnatural amino acids Fmoc-triazine-amino acids; antibacterials; short peptidomimetics; intracellular targeting; unnatural amino acids
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MDPI and ACS Style

Gunasekaran, P.; Kim, E.Y.; Lee, J.; Ryu, E.K.; Shin, S.Y.; Bang, J.K. Synthesis of Fmoc-Triazine Amino Acids and Its Application in the Synthesis of Short Antibacterial Peptidomimetics. Int. J. Mol. Sci. 2020, 21, 3602.

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