A series of amino acid and dipeptide prodrugs of IMB-070593, a fluoroquinolone candidate discovered in our lab, were synthesized and evaluated for their water solubility and then antibacterial activity. Our results reveal that four amino acid prodrugs 4a,b,e,f and two dipeptide prodrugs 4k,l have much greater solubility (>85 mg/mL) than IMB-070593 mesylate (22.5 mg/mL). Compounds 4a and 4k show...

Synthetic dipeptides comprising mixtures of enantiomers, diastereomers, or sequential isomers were converted into their N-perfluoroacetyl dipeptide esters (perfluoroacetyl: trifluoroacetyl, pentafluoroacetyl, heptafluorobutyryl; ester: methyl, 1-propyl, 2-propyl, 2,2,2-trifluoroethyl) and analyzed by GC-MS on the chiral stationary phases Chirasil-L-Val and Lipodex-E using helium as carrier gas....

In this presentation, we describe an integrated approach for the molecular basis for sweet taste among dipeptide-based ligands. By comparing the results obtained from X-ray diffraction studies with the conformations from NMR analysis and molecular modeling, we have observed recurring topochemical motifs that agree with previous models for sweet taste. In our examination of the unexplored D zone...

Two novel, asymmetric methanofullerenes are presented, which self-assemble in cyclohexane upon thermal cycling to 80 °C. We show that, through the introduction of a dipeptide sequence to one terminus of the dendritic methanofullerene, it is possible to transform the assembly behavior of these molecules from poorly formed aggregates to high-aspect-ratio nanorods. These nanorods have diameters of...

Time-resolved CIDNP and Laser Flash Photolysis have been applied to the investigation of the kinetics and mechanism of CIDNP formation in the reactions of aza-aromatic dye 2,2′-dipyridyl and protein-related molecules, including N-acetyl derivatives of three amino acids (tryptophan, tyrosine, histidine) the dipeptide tryptophan-tyrosine, and hen egg-white lysozyme in native and denatured states....

The synthesis and biological activity of new conjugates of muramyl dipeptide (MDP) and nor-muramyl dipeptide (nor-MDP) with tuftsin and retro-tuftsin derivatives containing isopeptide bond between ε-amino group of lysine and carboxyl group of simple amino acids such as Ala, Gly and Val are presented. We presumed, based on the cytokine profile, that the examined conjugates of tuftsin and MDP wer...

A syntheses of three new muramyl dipeptide (MDP) analogues related to LK 423 as potential immunomodulators are presented. The dipeptide part of the lead compound was modified by introducing a phosphonamide isostere instead of the amide bond between Lalanine and D-glutamic acid (or D-isoglutamine), yielding new MDP analogues 5 and 9. Furthermore, the amide bond between L-Ala and D-Glu was replac...

Muramyl dipeptide, N-acetylmuramyl-L-alanyl-D-isoglutamine, induced adjuvant arthritis in WKA rats when injected in a water-in-oil emulsion prepared with Freund incomplete adjuvant (Difco), but not when emulsified with Drackeol and Arlacel A.