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Chemo-enzymatic Synthesis of N-glycans for Array Development and HIV Antibody Profiling
Published on: February 5, 2018
Chemoenzymatic synthesis of oligohyaluronan-lipid conjugates
Dipali Ruhela1, Saul Kivimäe, Francis C Szoka
1Departments of Bioengineering, Therapeutic Sciences, and Pharmaceutical Chemistry, University of California San Francisco , 513 Parnassus Avenue, San Francisco, California 94143-0912, United States.
Abstract:
Herein, we describe an efficient and high-yielding method to synthesize hyaluronan oligosaccharide-lipid conjugates. This strategy is based on first covalently attaching diphytanoyl glycerophosphatidylethanolamine (DiPhPE) to commercially available high molecular weight hyaluronic acid (HA), via the carboxylate group of the glucuronic acid using carbodiimide chemistry. The HA-lipid conjugate mixture is then digested with bovine testicular hyaluronidase to yield HA-DiPhPE conjugates that have a narrow distribution of moderately sized HA oligosaccharides. These HA-lipid conjugates can be incorporated into liposomes or micelles to selectively target CD44 that is overexpressed on many cancer or cancer initiating cells.
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