標題: Single-Step Per-O-Sulfonation of Sugar Oligomers with Concomitant 1,6-Anhydro Bridge Formation for Binding Fibroblast Growth Factors
作者: Yeh, Che-Jui
Ku, Chiao-Chu
Lin, Wei-Chen
Fan, Chiao-Yuan
Zulueta, Medel Manuel L.
Manabe, Yoshiyuki
Fukase, Koichi
Li, Yaw-Kuen
Hung, Shang-Cheng
應用化學系
Department of Applied Chemistry
關鍵字: anhydrosugars;carbohydrates;fibroblast growth factors;oligosaccharides;per-O-sulfonation;synthetic methods
公開日期: 18-Jan-2019
摘要: Many circulating cancer-related proteins, such as fibroblast growth factors (FGFs), associate with glycosaminoglycans-particularly heparan sulfate-at the cell surface. Disaccharide analogues of heparan sulfate had previously been identified as the shortest components out of the sugars that bind to FGF-1 and FGF-2. Taking note of the typical pose of l-iduronic acid, we conceived of per-O-sulfonated analogues of such disaccharides, and devised a single-step procedure for per-O-sulfonation of unprotected sugars with concomitant 1,6-anhydro bridge formation to achieve such compounds through direct use of SO3Et3N as sulfonation reagent and dimethylformamide as solvent. The synthesized sugars based on the oligomaltose backbone bound FGF-1 and FGF-2 mostly at the sub-micromolar level, although the tetrasaccharide analogue achieved low-nanomolar binding with FGF-2.
URI: http://dx.doi.org/10.1002/cbic.201800464
http://hdl.handle.net/11536/148819
ISSN: 1439-4227
DOI: 10.1002/cbic.201800464
期刊: CHEMBIOCHEM
Volume: 20
起始頁: 237
結束頁: 240
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