Evidence for a heparin derivative containing an N-sulfated aziridine ring that retains high anti-factor Xa activity

A derivative of heparin 2 containing a high proportion of N-sulfated aziridine groups within the aminosugar units has been prepared from a chemically modified heparin 1 which contained the predominant repeat, → 4)-2-deoxy-2-sulfamino-α-d-glucose-3,6-bis sulfate-(1 → 4)-α-l-iduronic acid-2,3-bis sulfate-(1 →, and has been structurally characterized by 1H and 13C NMR employing COSY, 1H coupled and decoupled HMQC, and FTIR spectroscopies. Compound 2 (16 kDa) exhibited high anti-factor Xa activity comparable to intact heparin as measured by end-point analysis.