Ho-Il Choi

Synthesis of irreversible HIV-1 protease inhibitors containing sulfonamide and sulfone as amide bond isosteres

Abstract Novel irreversible HIV-1 protease inhibitors containing sulfonamide and sulfone as amide bond isosteres were designed, synthesized, and kinetically characterized. A representative compound 2 displayed rapid, time-dependent inactivation of HIV-1 protease and high potency in cell culture with IC50 of 6.6 nM.

Design and efficient synthesis of novel ascorbyl conjugated peptide with high collagen biosynthesis stimulating effects.

Collagen is critical for skin strength and elasticity, and its degradation leads to wrinkles that accompany aging. Based emphasis on the aesthetics, we tried to make a new compound that can highly stimulate collagen biosynthesis and synthesized ascorbyl conjugated peptide that is a complex form connected by succinoyl linker. We conducted several in vitro and in vivo experiments to identify if the compound has a potent activity, comparing to the ascorbic acid only for collagen biosynthesis. Our in vitro and in vivo result identified that ascorbyl conjugated peptide can stimulate collagen biosynthesis in human dermis and is assumably stable in the rat skin extracts. In conclusion, we strongly suggest that ascorbyl conjugated peptide can be used as a main ingredient for cosmetic products as well as wound healing agents.

NMR and topochemical studies of peptidomimetic HIV-I protease inhibitors containing a cis-epoxide amide isostere

NMR and topochemical studies of irreversible HIV-1 protease inhibitors containing a cis-epoxide as amide isostere have been carried out to identify conformational preference of the inhibitors in solution. The inhibitors prefer to adopt extended conformations similar to the beta-strand in solution.

β-Methanesulfonyl-L-valine as a novel, unnatural amino acid surrogate for P2 in the design of HIV protease inhibitors.

Abstract β-Methanesulfonyl-L-valine as a surrogate for asparagine and valine was designed, synthesized, and characterized. A representative compound 1 showed IC50 of 4.9 nM.