دورية أكاديمية
Chemoenzymatic synthesis and structural characterization of 2-O-sulfated glucuronic acid-containing heparan sulfate hexasaccharides
| العنوان: | Chemoenzymatic synthesis and structural characterization of 2-O-sulfated glucuronic acid-containing heparan sulfate hexasaccharides |
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| المؤلفون: | Hsieh, Po-Hung, Xu, Yongmei, Keire, David A, Liu, Jian |
| المصدر: | Glycobiology, 24(8) |
| سنة النشر: | 2014 |
| المجموعة: | Carolina Digital Repository (UNC - University of North Carolina) |
| مصطلحات موضوعية: | glucuronic acid 2-sulfate, Molecular Sequence Data, Sulfotransferases, Carbohydrate Conformation, Magnetic Resonance Spectroscopy, Heparitin Sulfate, chemoenzymatic synthesis, Glucuronates, sulfotransferase, heparan sulfate, Oligosaccharides, heparin |
| الوصف: | Heparan sulfate and heparin are highly sulfated polysaccharides that consist of a repeating disaccharide unit of glucosamine and glucuronic or iduronic acid. The 2-O-sulfated iduronic acid (IdoA2S) residue is commonly found in heparan sulfate and heparin; however, 2-O-sulfated glucuronic acid (GlcA2S) is a less abundant monosaccharide (∼<5% of total saccharides). Here, we report the synthesis of three GlcA2S-containing hexasaccharides using a chemoenzymatic approach. For comparison purposes, additional IdoA2S-containing hexasaccharides were synthesized. Nuclear magnetic resonance analyses were performed to obtain full chemical shift assignments for the GlcA2S- and IdoA2S-hexasaccharides. These data show that GlcA2S is a more structurally rigid saccharide residue than IdoA2S. The antithrombin (AT) binding affinities of a GlcA2S- and an IdoA2S-hexasaccharide were determined by affinity co-electrophoresis. In contrast to IdoA2S-hexasaccharides, the GlcA2S-hexasaccharide does not bind to AT, confirming that the presence of IdoA2S is critically important for the anticoagulant activity. The availability of pure synthetic GlcA2S-containing oligosaccharides will allow the investigation of the structure and activity relationships of individual sites in heparin or heparan sulfate. |
| نوع الوثيقة: | article in journal/newspaper |
| اللغة: | English |
| العلاقة: | https://doi.org/10.17615/s7m5-5203Test; https://cdr.lib.unc.edu/downloads/rr1724749?file=thumbnailTest; https://cdr.lib.unc.edu/downloads/rr1724749Test |
| DOI: | 10.17615/s7m5-5203 |
| الإتاحة: | https://doi.org/10.17615/s7m5-5203Test https://cdr.lib.unc.edu/downloads/rr1724749?file=thumbnailTest https://cdr.lib.unc.edu/downloads/rr1724749Test |
| حقوق: | http://rightsstatements.org/vocab/InC/1.0Test/ |
| رقم الانضمام: | edsbas.4452450C |
| قاعدة البيانات: | BASE |
| DOI: | 10.17615/s7m5-5203 |
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