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Glycobiology, 1999, Vol. 9, No. 12 1331-1336
© 1999 Oxford University Press

A novel strategy to generatebiologically active neo-glycosaminoglycan conjugates

Jianhui Rong, Kerstin Nordling2, Ingemar Björk2 and Ulf Lindahla

Department of Medical Biochemistry and Microbiology, Box582, The Biomedical Center, Uppsala University, S-751 23 Uppsala,Sweden and 2Department of VeterinaryMedical Chemistry, Box 575, The Biomedical Center, The Swedish Universityof Agricultural Science, S-751 23 Uppsala, Sweden

Heparin and heparan sulfate are structurally related polysaccharideswith a variety of biological effects/functions. Most ofthese effects are due to interactions, of varying specificity, betweenthe negatively charged polysaccharide chains and proteins. Whilesuch interactions generally involve a single saccharide domain of decasaccharidesize or less, ternary complexes of two protein molecules bindingto separate domains on a single polysaccharide chain are known tooccur. To facilitate studies on domain organization and its importancefor biological function a strategy was developed to chemically conjugatedefined heparin oligomers in linear and chemoselective fashion.The procedure requires that the oligosaccharide to provide the reducing-terminaldomain of the conjugate is generated by lyase degradation of a parentpolysaccharide, whereas the nonreducing-terminal domain is obtainedthrough deaminative cleavage with nitrous acid. The applicabilityof the method was demonstrated by constructing a conjugate composedof two heparin 12-mers, of which the reducing-terminal componentcontained the antithrombin-binding region, whereas the nonreducing-terminaldomain did not. Contrary to any of the unconjugated oligomers, theproduct was found to efficiently promote the inactivation of thrombinby antithrombin.

a Towhom correspondence should be addressed.


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Biological Effects of Heparan Sulfates and Regioselectively Modified Heparin-Heparan Mimetics
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