The DOI matches its Crossref record; 1 of the 1 references it cites were found in a registry or an index.
Tryptophan 7-Halogenase (PrnA) Structure Suggests a Mechanism for Regioselective Chlorination
Open accessAbstract
Chlorinated natural products include vancomycin and cryptophycin A. Their biosynthesis involves regioselective chlorination by flavin-dependent halogenases. We report the structural characterization of tryptophan 7-halogenase (PrnA), which regioselectively chlorinates tryptophan. Tryptophan and flavin adenine dinucleotide (FAD) are separated by a 10 angstrom–long tunnel and bound by distinct enzyme modules. The FAD module is conserved in halogenases and is related to flavin-dependent monooxygenases. On the basis of biochemical studies, crystal structures, and by analogy with monooxygenases, we predict that FADH 2 reacts with O 2 to make peroxyflavin, which is decomposed by Cl – . The resulting HOCl is guided through the tunnel to tryptophan, where it is activated to participate in electrophilic aromatic substitution.
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Messerschmidt, A., Prade, L., & Wever, R. (1997) · Biological Chemistry · doi:10.1515/bchm.1997.378.3-4.309 · Cited by 275
Cited by
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van Berkel, W. J. H., Kamerbeek, N. M., & Fraaije, M. W. (2006) · Journal of Biotechnology · doi:10.1016/j.jbiotec.2006.03.044 · Cited by 671
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Zhang, M., Wang, L., & Zhong, D. (2017) · Archives of Biochemistry and Biophysics · doi:10.1016/j.abb.2017.08.007 · Cited by 115
Dynamics and mechanisms of DNA repair by photolyase
Liu, Z., Wang, L., & Zhong, D. (2015) · Physical Chemistry Chemical Physics · doi:10.1039/c4cp05286b · Cited by 86
Halogenase engineering and its utility in medicinal chemistry
Fraley, A. E., & Sherman, D. H. (2018) · Bioorganic & Medicinal Chemistry Letters · doi:10.1016/j.bmcl.2018.04.066 · Cited by 45
Jiang, Y., Snodgrass, H. M., Zubi, Y. S., Roof, C. V., Guan, Y., Mondal, D., Honeycutt, N. H., Lee, J. W., Lewis, R. D., Martinez, C. A., et al. (2022) · Angewandte Chemie International Edition · doi:10.1002/anie.202214610 · Cited by 44
Metadata
- Authors
- Dong, C., Flecks, S., Unversucht, S., Haupt, C., van Pée, K.-H., & Naismith, J. H.
- Venue
- Science
- Published
- 2005-09-30
- Volume
- 309
- Issue
- 5744
- Pages
- 2216-2219
- ISSN
- 0036-8075 (ISSN-L)
- 1095-9203
- OpenAlex
- W2163839853
- Cited by
- 398
- References
- 1
- FWCI
- 13.19
- Type
- journal article
- Language
- en
- Open access
- green
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