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- W2122689098 endingPage "9249" @default.
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- W2122689098 abstract "The conformation of d-alanine (d-Ala) groups of bacterial teichoic acid is a central, yet untested, paradigm of microbiology. The d-Ala binds via the C-terminus, thereby allowing the amine to exist as a free cationic NH3+ group with the ability to form a contact ion pair with the nearby anionic phosphate group. This conformation hinders metal chelation by the phosphate because the zwitterion pair is charge neutral. To the contrary, the repulsion of cationic antimicrobial peptides (CAMPs) is attributed to the presence of the d-Ala cation; thus the ion pair does not form in this model. Solid-state nuclear magnetic resonance (NMR) spectroscopy has been used to measure the distance between amine and phosphate groups within cell wall fragments of Bacillus subtilis. The bacteria were grown on media containing 15N d-Ala and β-chloroalanine racemase inhibitor. The rotational-echo double-resonance (REDOR) pulse sequence was used to measure the internuclear dipolar coupling, and the results demonstrate (1) the metal-free amine-to-phosphate distance is 4.4 Å and (2) the amine-to-phosphate distance increases to 5.4 Å in the presence of Mg2+ ions. As a result, the zwitterion exists in a nitrogen−oxygen ion pair configuration providing teichoic acid with a positive charge to repel CAMPs. Additionally, the amine of d-Ala does not prevent magnesium chelation in contradiction to the prevailing view of teichoic acids in metal binding. Thus, the NMR-based description of teichoic acid structure resolves the contradictory models, advances the basic understanding of cell wall biochemistry, and provides possible insight into the creation of new antibiotic therapies." @default.
- W2122689098 created "2016-06-24" @default.
- W2122689098 creator A5021150846 @default.
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- W2122689098 creator A5053317752 @default.
- W2122689098 creator A5057194990 @default.
- W2122689098 creator A5085056101 @default.
- W2122689098 date "2009-09-11" @default.
- W2122689098 modified "2023-09-25" @default.
- W2122689098 title "Conformation of the Phosphate <scp>d</scp>-Alanine Zwitterion in Bacterial Teichoic Acid from Nuclear Magnetic Resonance Spectroscopy" @default.
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- W2122689098 doi "https://doi.org/10.1021/bi900503k" @default.
- W2122689098 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/4196936" @default.