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Crystal Structures of Salinosporamide A (NPI-0052) and B (NPI-0047) in Complex with the 20S Proteasome Reveal Important Consequences of β-Lactone Ring Opening and a Mechanism for Irreversible Binding
Abstract
The crystal structures of the yeast 20S proteasome core particle (CP) in complex with Salinosporamides A (NPI-0052; 1) and B (4) were solved at <3 angstroms resolution. Each ligand is covalently bound to Thr1O(gamma) via an ester linkage to the carbonyl derived from the beta-lactone ring of the inhibitor. In the case of 1, nucleophilic addition to the beta-lactone ring is followed by addition of C-3O to the chloroethyl group, giving rise to a cyclic ether. The crystal structures were compared to that of the omuralide/CP structure solved previously, and the collective data provide new insights into the mechanism of inhibition and irreversible binding of 1. Upon opening of the beta-lactone ring, C-3O assumes the position occupied by a water molecule in the unligated enzyme and hinders deacylation of the enzyme-ligand complex. Furthermore, the resulting protonation state of Thr1NH2 deactivates the catalytic N-terminus.
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Chauhan, D., Catley, L., Li, G., Podar, K., Hideshima, T., Velankar, M., Mitsiades, C., Mitsiades, N., Yasui, H., Letai, A., et al. (2005) · Cancer Cell · doi:10.1016/j.ccr.2005.10.013 · Cited by 694
Groll, M., Kim, K. B., Kairies, N., Huber, R., & Crews, C. M. (2000) · Journal of the American Chemical Society · doi:10.1021/ja993588m · Cited by 304
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Metadata
- Authors
- Groll, M., Huber, R., & Potts, B. C. M.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2006-03-24
- Volume
- 128
- Issue
- 15
- Pages
- 5136-5141
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2069992059
- Cited by
- 312
- References
- 2
- FWCI
- 9.95
- Type
- journal article
- Language
- en
- Open access
- closed
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- Groll, M., Huber, R., & Potts, B. C. M. (2006). Crystal Structures of Salinosporamide A (NPI-0052) and B (NPI-0047) in Complex with the 20S Proteasome Reveal Important Consequences of β-Lactone Ring Opening and a Mechanism for Irreversible Binding. Journal of the American Chemical Society. https://doi.org/10.1021/ja058320b
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