Sulfated Oligosaccharides Isolated from the Deamination Products of Heparins1

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Abstract
Porcine heparin, whale heparin, and a solvolyzed porcine heparin were deaminated, and sulfated oligosaccharides, compounds 3f, 4f, 3a, 4a, 5, 6, 7a, 10, 11f, 11a, and 13 were isolated from the deamination products by Dowex 1x2 (Cl- form) column chromatography and high voltage paper electrophoresis and/or gel filtration on Sephadex G-25. Based on the results of chemical, 1H and 13C NMR spectral analyses, and of Smith degradation, together with previous observations, the structures of these sulfated oligosaccharides are proposed to be as follows: compound 3f, IdUA(2S)α1↑4GlcNAcα1↑4GlcUA; compound 4f, IdUAα1↑4GlcNAc(6S)α1↑4GlcUA; compound 3a, IdUA(2S)α1↑4GlcNAcα1↑4GIcUA; compound 4f, IdUAα1↑4GlcNAc(6S)α1↑4GlcUA;compound 3a, IdUA(2S)α1↑4GlcNAcα1↑4GlcUAβ1↑4aMan; compound 4a, IdUAα1↑4GlucNAc(6S)α1↑4GlcUAβ1↑4aMan; compound 5, IdUA(2S)α1↑4aMan; compound 6, GlcUAβ1↑4aMan(6S); compound 7a, IdUAα1↑4aMan(6S); compound 10, IdUA(2S)α1↑4GlcNAc(6S)alpha;1↑4GlcUAβ1↑4aMan; compound 11f, IdUA(2S)α1↑4GIcNAcα1↑4GlcUAβ1↑4aMan(6S); compound 115, IdUAα1↑4GlcNAc{6S)α1↑4GlcUAβ1↑4aMan(6S); compound 13, IdUA(2S)α1↑4aMan(6S). For the sulfated disaccharides, the same results as those reported in our previous papers were obtained. On the other hand, the proportion of total sulfated tri- and tetrasaccharides from whale heparin was 1.9 times higher than that from porcine heparine, reflecting a higher content of GlcNAc in the former. Also, the yields of compound 11a from these two heparins were comparable to their anticoagulant activities. In addition, certain 2-O-sulfates on IdUA flanked with GIcNS(6X) (X=H or S) in the heparin molecule are suggested to be important for the activity.