Synthesis and evaluation of aziridine and symmetry-based epoxide affinity labels for HIV-1 protease

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 μM to 10 nM).

Name thesis:degree_name

Ph.D.

Level thesis:degree_level

Dissertation

Discipline thesis:degree_discipline

Chemistry

Grantor

University of Illinois at Urbana-Champaign

Year dc:date

2011

Author dc:creator

• Kreps, James Jonathan

Contributors dc:contributor

• Katzenellenbogen, John A.

• Chemistry, Organic
• Chemistry, Pharmaceutical

Statement dc:rights

• Copyright 1996 Kreps, James Jonathan

Language dc:language

eng

Identifier

9780591198690
AAI9712337
(UMI)AAI9712337

OAI identifier oai:identifier

oai:www.ideals.illinois.edu:2142/20034