Lysine Scanning of Arg10 -Teixobactin: Deciphering the Role of Hydrophobic and Hydrophilic Residues

ACS Omega
Shimaa A H Abdel MonaimFernando Albericio

Abstract

Teixobactin is a recently discovered antimicrobial cyclodepsipeptide with good activity against Gram positive bacteria. Taking Arg10-teixobactin as a reference, where the nonproteinogenic residue l-allo-enduracididine was substituted by arginine, a lysine scan was performed to identify the importance of keeping the balance between hydrophilic and hydrophobic amino acids for the antimicrobial activities of this peptide family. Thus, the substitution of four isoleucine residues present in the natural sequence by lysine led to a total loss of activity. On the other hand, the substitution of the polar noncharged residues and alanine by lysine allowed us to keep and in some cases to improve the antimicrobial activity.

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Citations

Nov 6, 2018·ChemMedChem·Shimaa A H Abdel MonaimFernando Albericio
Oct 11, 2019·Medicinal Research Reviews·Xiaoshu Jing, Kang Jin
Mar 10, 2020·ChemMedChem·Clinton G L Veale, Ronel Müller
Jul 5, 2017·Natural Product Reports·Anna MüllerTanja Schneider
Sep 29, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Shimaa A H Abdel MonaimBeatriz G de la Torre
Oct 11, 2017·Chemistry : a European Journal·Chuchu GuoQi Zhang
Oct 3, 2017·Chemical Communications : Chem Comm·K H ChenJ S Nowick
Jul 28, 2018·Frontiers in Microbiology·Estelle J RamchuranLinda A Bester
Sep 26, 2019·Chembiochem : a European Journal of Chemical Biology·Sorina ChioreanJohn C Vederas
Dec 4, 2019·Annals of the New York Academy of Sciences·John A KarasTony Velkov
Jun 7, 2020·Nature Communications·Rhythm ShuklaMarkus Weingarth
Aug 28, 2020·Frontiers in Chemistry·Victor V YimMargaret A Brimble
Oct 11, 2017·Organic & Biomolecular Chemistry·Christian E SchumacherMargaret A Brimble
Sep 14, 2018·Chemical Science·Po-Chao WenEmad Tajkhorshid
Jan 6, 2021·Medicine in Drug Discovery·Gregory UpertPhilipp Ermert
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Aug 11, 2017·Journal of Medicinal Chemistry·Shimaa A H Abdel MonaimBeatriz G de la Torre
Feb 12, 2020·ACS Chemical Biology·Michael A MorrisJames S Nowick
Oct 9, 2018·Journal of the American Chemical Society·Hyunjun YangJames S Nowick
Jan 24, 2018·The Journal of Organic Chemistry·Dhanaraju MandalapuQi Zhang

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