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• W2007753612 abstract "An analogue of the antithrombin-III-binding region of heparin has been synthesized. This analogue [GlcNSO3 (6-OSO3)-GlcU-GlcNSO3 (3,6-OSO3)-Xyl(2-OSO3)-GlcNSO3 (6-OSO3), i.e. compound 11] lacks the carboxylate function of the α-L-iduronic acid moiety, which implies that the 2-O-sulphated α-L-idopyranuronate unit is replaced by 2-O-sulphated β-D-xylopyranose. Compound 11 was prepared from fully protected pentasaccharide 10a, which was synthesized from two disaccharides (7 and 6b) and a monosaccharide (9). Synthesis of disaccharide 6b required preparation of a new, suitably protected xylopyranose-building block: 2-O-acetyl- or 2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-α-D-xylopyranosyl fluoride 4a,b.High-field NMR spectroscopy of compound 11 afforded a complete set of interproton coupling data and Nuclear Overhauser Enhancement data, which have been used for conformational analysis. It appears that β-D-xylopyranose in compound 11 adopts exclusively the 4C1 conformation, whereas it is known that α-L-idopyranuronate in the naturally occurring heparin fragment exhibits 2S0 and 1C4 conformations. Thus, the carboxylate function of α-L-idopyranuronate in the heparin fragment is an important conformational drive.Since neither compound 11 nor another analogue containing L-idose (with similar conformational properties as the natural fragment) elicit AT-III-mediated activity, it is proposed that the carboxylate of idopyranuronate interacts with AT-III to bring about the active conformation of the protease inhibitor." @default.
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• W2007753612 date "2010-09-02" @default.
• W2007753612 modified "2023-09-24" @default.
• W2007753612 title "Synthesis and conformational analysis of an analogue of the antithrombin-binding region of heparin: The role of the carboxylate function of α-L-idopyranuronate" @default.
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• W2007753612 doi "https://doi.org/10.1002/recl.19871061107" @default.
• W2007753612 hasPublicationYear "2010" @default.
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