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Mechanisms of Coenzyme B 12 -Dependent Rearrangements
Abstract
Coenzyme B 12 serves as a cofactor in various enzymatic reactions in which a hydrogen atom is interchanged with a substituent on an adjacent carbon atom. Measurement of the dissociation energy of the coenzyme's cobalt-carbon bond and studies of the rearrangement of model free radicals related to those derived from methylmalonyl-coenzyme A suggest that these enzymatic reactions occur through homolytic dissociation of the coenzyme's cobalt-carbon bond, abstraction of a hydrogen atom from the substrate by the coenzyme-derived 5′-deoxyadenosyl radical, and rearrangement of the resulting substrate radical. The only role thus far identified for coenzyme B 12 in these reactions—namely, that of a free radical precursor—reflects the weakness, and facile dissociation, of the cobalt-carbon bond.
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Cited by
Electrostatic Basis for Enzyme Catalysis
Warshel, A., Sharma, P. K., Kato, M., Xiang, Y., Liu, H., & Olsson, M. H. M. (2006) · Chemical Reviews · doi:10.1021/cr0503106 · Cited by 1,444
Vitamin B12: Experiments Concerning the Origin of Its Molecular Structure
Eschenmoser, A. (1988) · Angewandte Chemie International Edition in English · doi:10.1002/anie.198800051 · Cited by 374
Quantum Chemical Studies of Radical-Containing Enzymes
Himo, F., & Siegbahn, P. E. M. (2003) · Chemical Reviews · doi:10.1021/cr020436s · Cited by 263
STUPPERICH, E., EISINGER, H. J., & KRÄUTLER, B. (1988) · European Journal of Biochemistry · doi:10.1111/j.1432-1033.1988.tb13910.x · Cited by 113
Yoshimura, A., Zimmers, T., Neumann, D., Longmore, G., Yoshimura, Y., & Lodish, H. F. (1992) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(19)49956-0 · Cited by 112
Metadata
- Authors
- Halpern, J.
- Venue
- Science
- Published
- 1985-02-22
- Volume
- 227
- Issue
- 4689
- Pages
- 869-875
- ISSN
- 0036-8075 (ISSN-L)
- 1095-9203
- OpenAlex
- W1972400761
- Cited by
- 496
- References
- 0
- FWCI
- 4.23
- Type
- journal article
- Language
- en
- Open access
- closed
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