Heungsik Yoon

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.

Synthesis of 1-β-amino-1-deoxynojirimycins: a new family of glucosidase inhibitors

Abstract The title compounds 7 and 8 , synthesized in one step from nojirimycin bisulfite adduct 3 , are of mechanistic and synthetic interest in the design of new glucosidase inhibitors.

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.

An efficient and enantioselective synthesis of a chiral primary amine

Abstract An efficient and enantioselective method for the preparation of a chiral primary amine has been developed. Starting from N-protected L or D-amino acid the sequence involves coupling with N-methoxy-N-methylamine, acylation, olefination with potassium bis(trimethylsilyl)amide, and hydrogenation.