The DOI matches its Crossref record; 31 of the 31 references it cites were found in a registry or an index.
N-Methylation of Amino Acids in Gelatinase Biosynthesis-Activating Pheromone Identifies Key Site for Stability Enhancement with Retention of the Enterococcus faecalis fsr Quorum Sensing Circuit Response
Abstract
The growing prevalence of multiantibiotic-resistant bacteria necessitates looking at potential alternative approaches for attenuating infections by bacteria while reducing the rate of antibiotic resistance development. Enterococcus faecalis is responsible for a large percentage of clinical enterococci infections, and its pathogenicity has been demonstrated to be influenced by quorum sensing (QS). In this study, we report the systematic study of the relationship between backbone hydrogens and the ability to activate the FsrC receptor. We demonstrate that N-methylation was particularly well-tolerated at one site (Phe7) and granted stability against protease digestion, increasing the peptide half-life relative to the native signal by more than 6-fold. The inclusion of the N-Me-Phe7 modification may be useful for improving the pharmacological properties of E. faecalis QS inhibitors as part of the development of future therapeutic candidates.
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Cites
The rise of the Enterococcus: beyond vancomycin resistance
Arias, C. A., & Murray, B. E. (2012) · Nature Reviews Microbiology · doi:10.1038/nrmicro2761 · Cited by 1,776
Anti-virulence strategies to combat bacteria-mediated disease
Rasko, D. A., & Sperandio, V. (2010) · Nature Reviews Drug Discovery · doi:10.1038/nrd3013 · Cited by 1,373
(2000) · Cited by 1,342
The ecology, epidemiology and virulence of Enterococcus
Fisher, K., & Phillips, C. (2009) · Microbiology · doi:10.1099/mic.0.026385-0 · Cited by 1,227
Advances in Fmoc solid‐phase peptide synthesis
Behrendt, R., White, P., & Offer, J. (2016) · Journal of Peptide Science · doi:10.1002/psc.2836 · Cited by 760
Multiple-Drug Resistant Enterococci: The Nature of the Problem and an Agenda for the Future
Huycke, M. M., Sahm, D. F., & Gilmore, M. S. (1998) · Emerging Infectious Diseases · doi:10.3201/eid0402.980211 · Cited by 718
Bacterial Quorum Sensing and Microbial Community Interactions
Abisado, R. G., Benomar, S., Klaus, J. R., Dandekar, A. A., & Chandler, J. R. (2018) · mBio · doi:10.1128/mbio.02331-17 · Cited by 674
N-Methylation of Peptides: A New Perspective in Medicinal Chemistry
Chatterjee, J., Gilon, C., Hoffman, A., & Kessler, H. (2008) · Accounts of Chemical Research · doi:10.1021/ar8000603 · Cited by 577
N‐Methylation of Peptides and Proteins: An Important Element for Modulating Biological Functions
Chatterjee, J., Rechenmacher, F., & Kessler, H. (2013) · Angewandte Chemie International Edition · doi:10.1002/anie.201205674 · Cited by 494
Qin, X., Singh, K. V., Weinstock, G. M., & Murray, B. E. (2001) · Journal of Bacteriology · doi:10.1128/jb.183.11.3372-3382.2001 · Cited by 253
Metadata
- Authors
- McBrayer, D. N., Gantman, B. K., & Tal-Gan, Y.
- Venue
- ACS Infectious Diseases
- Publisher
- American Chemical Society (ACS)
- Published
- 2019-04-11
- Volume
- 5
- Issue
- 6
- Pages
- 1035-1041
- ISSN
- 2373-8227
- Cited by
- 18
- References
- 31
- Language
- en
- Licence
- Funders
- Division of Chemistry (CHE-1808370)
- National Institute of General Medical Sciences (R35GM128651, GM103440)
- Cayman Biomedical Research Institute
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- CoChat. (2026). Citation check: N-Methylation of Amino Acids in Gelatinase Biosynthesis-Activating Pheromone Identifies Key Site for Stability Enhancement with Retention of the Enterococcus faecalis fsr Quorum Sensing Circuit Response. https://app.cochat.ai/papers/10.1021/acsinfecdis.9b00097
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- McBrayer, D. N., Gantman, B. K., & Tal-Gan, Y. (2019). N-Methylation of Amino Acids in Gelatinase Biosynthesis-Activating Pheromone Identifies Key Site for Stability Enhancement with Retention of the Enterococcus faecalis fsr Quorum Sensing Circuit Response. ACS Infectious Diseases. https://doi.org/10.1021/acsinfecdis.9b00097
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