Synthesis and characterization of carbohydrate-based biosurfactant mimetics.

Glycolipid biosurfactants are of interest for various industry sectors. We report the synthesis and characterization of enantiopure poly-amido-saccharides (PASs) containing myristoyl (C14), palmitoyl (C16), or stearoyl (C18) terminal chain lengths as mimetics of glycolipid biosurfactants. These amphiphilic polymers are water soluble, adopt a helical secondary structure, decompose at temperatures greater than 240 °C, are non-cytotoxic, and self-assemble into nanostructures.

Beyond nylon 6: polyamides ring opening polymerization of designer lactam monomers for biomedical applications.

Ring opening polymerization (ROP) of lactams is a highly efficient and versatile method to synthesize polyamides. Within the last ten years, significant advances in polymerization methodology and monomer diversity are ushering in a new era of polyamide chemistry. We begin with a discussion of polymerization techniques including the most widely used anionic ring opening polymerization (AROP), and less prevalent cationic ROP and enzyme-catalyzed ROP.

Synthesis and Characterization of Regioselectively Functionalized Mono-Sulfated and -Phosphorylated Anionic Poly-Amido-Saccharides.

Polysaccharides are abundant in nature and employed in various biomedical applications ranging from scaffolds for tissue engineering to carriers for drug delivery systems. However, drawbacks such as tedious isolation protocols, contamination, batch-to-batch consistency, and lack of compositional control with regards to stereo- and regioselectivity impede the development and utility of polysaccharides, and thus mimetics are highly sought after. We report a synthetic strategy to regioselectively functionalize poly-amido-saccharides with sulfate or phosphate groups using post-polymerization modification reactions.

Sulfated poly-amido-saccharides (sulPASs) are anticoagulants and .

Anticoagulant therapeutics are a mainstay of modern surgery and of clotting disorder management such as venous thrombosis, yet performance and supply limitations exist for the most widely used agent - heparin. Herein we report the first synthesis, characterization, and performance of sulfated poly-amido-saccharides (sulPASs) as heparin mimetics. sulPASs inhibit the intrinsic pathway of coagulation, specifically FXa and FXIa, as revealed by human plasma clotting assays and serine protease inhibition assays.

Synthesis of dimeric analogs of adenophostin A that potently evoke Ca release through IP receptors.

Inositol 1,4,5-trisphosphate receptors (IPRs) are tetrameric intracellular channels through which many extracellular stimuli initiate the Ca signals that regulate diverse cellular responses. There is considerable interest in developing novel ligands of IPR. Adenophostin A (AdA) is a potent agonist of IPR and since some dimeric analogs of IPR ligands are more potent than the corresponding monomer; we considered whether dimeric AdA analogs might provide agonists with increased potency.