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Chemoenzymatic Synthesis of Homogeneous Ultralow Molecular Weight Heparins
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Chemoenzymatic Synthesis of Homogeneous Ultralow Molecular Weight Heparins
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Journal Article
Chemoenzymatic Synthesis of Homogeneous Ultralow Molecular Weight Heparins
2011
Overview
Ultralow molecular weight (ULAAW) heparins are sulfated glycans that are clinically used to treat thrombotic disorders. ULMW heparins range from 1500 to 3000 daltons, corresponding from 5 to 10 saccharide units. The commercial drug Arixtra (fondaparinux sodium) is a structurally homogeneous ULMW heparin pentasaccharide that is synthesized through a lengthy chemical process. Here, we report 10- and 12-step chemoenzymatic syntheses of two structurally homogeneous ULMW heparins (MW = 1778.5 and 1816.5) in 45 and 37% overall yield, respectively, starting from a simple disaccharide. These ULMW heparins display excellent in vitro anticoagulant activity and comparable pharmacokinetic properties to Arixtra, as demonstrated in a rabbit model. The chemoenzymatic approach is scalable and shows promise for a more efficient route to synthesize this important class of medicinal agent.
Publisher
American Association for the Advancement of Science,The American Association for the Advancement of Science
Subject
/ Anticoagulants - chemical synthesis
/ Anticoagulants - pharmacokinetics
/ Anticoagulants - pharmacology
/ Biological and medical sciences
/ Blood. Blood coagulation. Reticuloendothelial system
/ drugs
/ Enzymes
/ Glycan
/ Glycosyltransferases - metabolism
/ Heparin
/ Heparin, Low-Molecular-Weight - chemical synthesis
/ Heparin, Low-Molecular-Weight - chemistry
/ Heparin, Low-Molecular-Weight - pharmacokinetics
/ Heparin, Low-Molecular-Weight - pharmacology
/ Heparins
/ N-Acetylglucosaminyltransferases - metabolism
/ Oligosaccharides - chemistry
/ Pharmacology. Drug treatments
/ Polysaccharides - pharmacokinetics
/ Polysaccharides - pharmacology
/ Protons
/ Rabbits
/ Racemases and Epimerases - metabolism
/ Sodium
/ Spectrometry, Mass, Electrospray Ionization
