The DOI matches its Crossref record.
Partitioning the Loss in Vancomycin Binding Affinity for d -Ala- d -Lac into Lost H-Bond and Repulsive Lone Pair Contributions
Abstract
The binding affinity of 4, which incorporates a methylene (CH2) in place of the key linking amide of Ac2-l-Lys-d-Ala-d-Ala, for vancomycin was compared with that of Ac2-l-Lys-d-Ala-d-Ala (3) and Ac2-l-Lys-d-Ala-d-Lac (5). The vancomycin affinity for 4 was approximately 10-fold less than that of 3, but 100-fold greater than that of 5. This suggests that the reduced binding affinity of 5 (4.1 kcal/mol) may be attributed to both the loss of a key H-bond (1.5 kcal/mol) and a destabilizing lone pair/lone pair electrostatic interaction introduced with the ester oxygen of 5 (2.6 kcal/mol) with the latter, not the H-bond, being responsible for the largest share of the 1000-fold reduction.
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Cited by
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Rossiter, S. E., Fletcher, M. H., & Wuest, W. M. (2017) · Chemical Reviews · doi:10.1021/acs.chemrev.7b00283 · Cited by 622
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O'Connell, K. M. G., Hodgkinson, J. T., Sore, H. F., Welch, M., Salmond, G. P. C., & Spring, D. R. (2013) · Angewandte Chemie International Edition · doi:10.1002/anie.201209979 · Cited by 435
Kell, A. J., Stewart, G., Ryan, S., Peytavi, R., Boissinot, M., Huletsky, A., Bergeron, M. G., & Simard, B. (2008) · ACS Nano · doi:10.1021/nn700183g · Cited by 320
Metadata
- Authors
- McComas, C. C., Crowley, B. M., & Boger, D. L.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2003-07-11
- Volume
- 125
- Issue
- 31
- Pages
- 9314-9315
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2052147832
- Cited by
- 166
- References
- 0
- FWCI
- 2.90
- Type
- journal article
- Language
- en
- Open access
- closed
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