Paz, S. et al. (2011) Tetrahydrobenzothiophene derivatives: conformationally restricted inhibitors of type II dehydroquinase. ChemMedChem, 6(2), pp. 266-272. (doi: 10.1002/cmdc.201000343)
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Publisher's URL: http://dx.doi.org/10.1002/cmdc.201000343
Abstract
Restriction is good for inhibition! Tetrahydrobenzothiophene-derived rigid mimics of the type II dehydroquinase (DHQ2)-catalyzed reaction intermediate are reported. These derivatives fix the interaction with the tyrosine, the base that initiates the enzymatic reaction, in an inappropriate orientation for catalysis. Two competitive inhibitors in the series, 2-propenyl derivative 5 e and 2-cyclopropylethyl compound 5 i (shown), were crystallized in complex with DHQ2 from <i>Helicobacter pylori</i>, and the X-ray structures were determined at 1.95Å and 1.85Å, respectively.
| Item Type: | Articles |
|---|---|
| Keywords: | Competitive inhibitors, Helicobacter pylori, Mycobacterium tuberculosis, restricted conformation, stable ozonides |
| Status: | Published |
| Refereed: | Yes |
| Glasgow Author(s) Enlighten ID: | Lapthorn, Dr Adrian |
| Authors: | Paz, S., Tizón, L., Otero, J.M., Llamas-Saiz, A.L., Fox, G.C., van Raaij, M.J., Lamb, H., Hawkins, A.R., Lapthorn, A.J., Castedo, L., and González-Bello, C. |
| Subjects: | Q Science > QD Chemistry |
| College/School: | College of Science and Engineering > School of Chemistry |
| Journal Name: | ChemMedChem |
| ISSN: | 1860-7179 |
| ISSN (Online): | 1860-7187 |
| Published Online: | 10 November 2010 |
| Related URLs: |
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