page_title: Heparin
section_title: Chemical
hierarchical_section_title: Heparin / Chemistry / Depolymerisation techniques / Chemical
caption_attribution_description: English: Reduction fig
context_page_description: Heparin, also known as unfractionated heparin, is a medication and naturally occurring glycosaminoglycan. As a medication it is used as an anticoagulant. Specifically it is also used in the treatment of heart attacks and unstable angina. It is given by injection into a vein or under the skin. Other uses include inside test tubes and kidney dialysis machines.
  Common side effects include bleeding, pain at the injection site, and low blood platelets. Serious side effects include heparin-induced thrombocytopenia. Greater care is needed in those with poor kidney function. Heparin appears to be relatively safe for use during pregnancy and breastfeeding. Heparin is produced by basophils and mast cells in all mammals.
  The discovery of heparin was announced in 1916. It is on the World Health Organization's List of Essential Medicines. A fractionated version of heparin, known as low molecular weight heparin, is also available.
context_section_description: Nitrous acid can be used to chemically depolymerise heparin/HS. Nitrous acid can be used at pH 1.5 or at a higher pH of 4. Under both conditions, nitrous acid effects deaminative cleavage of the chain. 
   At both 'high' (4) and 'low' (1.5) pH, deaminative cleavage occurs between GlcNS-GlcA and GlcNS-IdoA, albeit at a slower rate at the higher pH. The deamination reaction, and therefore chain cleavage, is regardless of O-sulfation carried by either monosaccharide unit.
  At low pH, deaminative cleavage results in the release of inorganic SO₄, and the conversion of GlcNS into anhydromannose (aMan). Low-pH nitrous acid treatment is an excellent method to distinguish N-sulfated polysaccharides such as heparin and HS from non N-sulfated polysacchrides such as chondroitin sulfate and dermatan sulfate, chondroitin sulfate and dermatan sulfate not being susceptible to nitrous acid cleavage.
caption: IdoA(2S)-aMan: The anhydromannose can be reduced to an anhydromannitol
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