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Molecular basis for vancomycin resistance in Enterococcus faecium BM4147: biosynthesis of a depsipeptide peptidoglycan precursor by vancomycin resistance proteins VanH and VanA
Abstract
Vancomycin resistance in Enterococcus faecium BM4147 is mediated by vancomycin resistance proteins VanA and VanH. VanA is a D-alanine:D-alanine ligase of altered substrate specificity [Bugg, T. D. H., Dutka-Malen, S., Arthur, M., Courvalin, P., & Walsh, C. T. (1991) Biochemistry 30, 2017-2021], while the sequence of VanH is related to those of alpha-keto acid dehydrogenases [Arthur, M., Molinas, C., Dutka-Malen, S., & Courvalin, P. (1991) Gene (submitted)]. We report purification of VanH to homogeneity, characterization as a D-specific alpha-keto acid dehydrogenase, and comparison with D-lactate dehydrogenases from Leuconostoc mesenteroides and Lactobacillus leichmanii. VanA was found to catalyze ester bond formation between D-alanine and the D-hydroxy acid products of VanH, the best substrate being D-2-hydroxybutyrate (Km = 0.60 mM). The VanA product D-alanyl-D-2-hydroxybutyrate could then be incorporated into the UDPMurNAc-pentapeptide peptidoglycan precursor by D-Ala-D-Ala adding enzyme from Escherichia coli or by crude extract from E. faecium BM4147. The vancomycin binding constant of a synthetic modified peptidoglycan analogue N-acetyl-D-alanyl-D-2-hydroxybutyrate (Kd greater than 73 mM) was greater than 1000-fold higher than the binding constant for N-acetyl-D-alanyl-D-alanine (Kd = 54 microM), partly due to the disruption of a hydrogen bond in the vancomycin-target complex, thus providing a molecular rationale for high-level vancomycin resistance.
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Cites
Bradford, M. M. (1976) · Analytical Biochemistry · doi:10.1016/0003-2697(76)90527-3 · Cited by 255,302
Structure, biochemistry and mechanism of action of glycopeptide antibiotics
Reynolds, P. E. (1989) · European Journal of Clinical Microbiology & Infectious Diseases · doi:10.1007/bf01967563 · Cited by 699
Cited by
The crisis in antibiotic resistance
Neu, H. C. (1992) · Science · doi:10.1126/science.257.5073.1064 · Cited by 2,834
Peptidoglycan structure and architecture
Vollmer, W., Blanot, D., & De Pedro, M. A. (2008) · FEMS Microbiology Reviews · doi:10.1111/j.1574-6976.2007.00094.x · Cited by 2,340
Antibiotic resistance and its cost: is it possible to reverse resistance?
Andersson, D. I., & Hughes, D. (2010) · Nature Reviews Microbiology · doi:10.1038/nrmicro2319 · Cited by 2,294
The antibiotic resistome: the nexus of chemical and genetic diversity
Wright, G. D. (2007) · Nature Reviews Microbiology · doi:10.1038/nrmicro1614 · Cited by 1,365
Self-citationVancomycin-Resistant Enterococci
Cetinkaya, Y., Falk, P., & Mayhall, C. G. (2000) · Clinical Microbiology Reviews · doi:10.1128/cmr.13.4.686 · Cited by 1,163
Metadata
- Authors
- Bugg, T. D. H., Wright, G. D., Dutka-Malen, S., Arthur, M., Courvalin, P., & Walsh, C. T.
- Venue
- Biochemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 1991-10-01
- Volume
- 30
- Issue
- 43
- Pages
- 10408-10415
- ISSN
- 0006-2960 (ISSN-L)
- 1520-4995
- OpenAlex
- W2153668434
- Cited by
- 650
- References
- 2
- FWCI
- 11.37
- Type
- journal article
- Language
- en
- Open access
- closed
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- CoChat. (2026). Citation check: Molecular basis for vancomycin resistance in Enterococcus faecium BM4147: biosynthesis of a depsipeptide peptidoglycan precursor by vancomycin resistance proteins VanH and VanA. https://app.cochat.ai/papers/10.1021/bi00107a007
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- Bugg, T. D. H., Wright, G. D., Dutka-Malen, S., Arthur, M., Courvalin, P., & Walsh, C. T. (1991). Molecular basis for vancomycin resistance in Enterococcus faecium BM4147: biosynthesis of a depsipeptide peptidoglycan precursor by vancomycin resistance proteins VanH and VanA. Biochemistry. https://doi.org/10.1021/bi00107a007
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Bibliographic data: Semantic Scholar, OpenAlex, Crossref.
Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.
