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oai:www.ideals.illinois.edu:2142/20034 2023-07-10 col_2142_5131 col_2142_14789 com_2142_5130 com_2142_14788 com_2142_8903

Katzenellenbogen, John A. Kreps, James Jonathan 2011-05-07T12:26:43Z 2011-05-07T12:26:43Z 10000-01-01 1996 Affinity labels have been prepared for HIV-1 protease. The synthesis of three symmetry-based epoxides and an aziridine analog of 1,2-epoxy-3-(p-nitrophenoxy)propane (EPNP) are reported. Assay procedures were developed to allow testing for both reversible and irreversible inhibition of HIV-1 protease, based on an internally-quenched fluorogenic substrate. Of eleven compounds assayed for reversible inhibition, five demonstrated modest to potent activities (K$\rm\sb{i}$'s ranging from 70 $\mu$M to 10 nM). Five compounds were tested for irreversible inhibition of the protease; of these, EPNP and three others were observed to inhibit the enzyme in a time-dependent manner consistent with irreversible inhibition. The aziridine analog of EPNP was found to be approximately fifteen times less potent than EPNP; two C$\sb2$ symmetric epoxides exhibited modes time-dependent inhibition of HIV-1 protease. Made available in DSpace on 2011-05-07T12:26:43Z (GMT). No. of bitstreams: 2 license.txt: 4922 bytes, checksum: 910b249b4beec47e7ab768910c8f966f (MD5) 9712337.pdf: 2995957 bytes, checksum: 2601b40f983bfe947a7606308cc0df16 (MD5) Previous issue date: 1996 Item marked as restricted to the 'UIUC Users [automated]' Group (id=2) by Howard Ding (hding2@illinois.edu) on 2011-05-07T14:41:06Z Item is restricted indefinitely. Restriction data tranferred 2014-07-01T11:17:44-05:00 Original Data Group with Access UIUC Users [automated] Release Date: none Reason: ETDs are only available to UIUC Users without author permission ETDs are only available to UIUC Users without author permission U of I Only 9780591198690 AAI9712337 (UMI)AAI9712337 http://hdl.handle.net/2142/20034 eng Copyright 1996 Kreps, James Jonathan Chemistry, Organic Chemistry, Pharmaceutical Synthesis and evaluation of aziridine and symmetry-based epoxide affinity labels for HIV-1 protease text Chemistry Chemistry University of Illinois at Urbana-Champaign Dissertation Ph.D.