Enoxaparin is a low molecular weight heparin with an average molecular weight of 4.5 kDa that is used as an anticoagulant. The first continuous flow process was developed to synthesize enoxaparin from heparin benzyl ester via base promoted partial depolymerization. Enoxaparin biosimilars were produced in a 25 minute residence time at 65° C in a commercially available flow system. Aqueous solutions of heparin benzyl ester and sodium hydroxide were pumped through the flow system at 0.24 mL/ min each, met at a t-mixer, and was pumped through reactor tubing which was heated by a hot oil bath to 55° C. The solution was dropped into 3X volume methanol and cassette dialysis was used for purification. NMR was employed for characterization. Flow chemistry was a useful technology for the preparation of Enoxaparin and in the future this method could be applied to the depolymerization of many glycosaminoglycans.
Author: Rebecca Brunner
Faculty Advisor: Richard T. Taylor, Department of Chemistry and Biochemistry
You must be logged in to post a comment.