Synthesis of seleno-fucose compounds and their application to the X-ray structural determination of carbohydrate-lectin complexes using single/multi-wavelength anomalous dispersion phasing
| Autor: | Hiromune Ando, Akihiro Imamura, Yosuke Nishikawa, Ryuichi Kato, Makoto Kiso, Hideharu Ishida, Hisayoshi Makyio, Tatsuya Suzuki, Junpei Shimabukuro, Masato Kawasaki |
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| Rok vydání: | 2017 |
| Předmět: |
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Molecular Diffraction Stereochemistry Clinical Biochemistry Pharmaceutical Science chemistry.chemical_element Crystallography X-Ray 010402 general chemistry 01 natural sciences Biochemistry Fucose Selenium chemistry.chemical_compound Lectins Drug Discovery Organometallic Compounds Multi-wavelength anomalous dispersion Molecular Biology Molecular Structure biology 010405 organic chemistry Organic Chemistry X-ray Lectin Carbohydrate 0104 chemical sciences Crystallography chemistry biology.protein Molecular Medicine SN2 reaction |
| Zdroj: | Bioorganic & Medicinal Chemistry. 25:1132-1142 |
| ISSN: | 0968-0896 |
| DOI: | 10.1016/j.bmc.2016.12.021 |
| Popis: | Selenium-incorporated fucoses (seleno-fucoses) differing in the position of the seleno-substituent were synthesized and applied to the X-ray structural determination of a carbohydrate-lectin complex using single/multi-wavelength anomalous dispersion (SAD/MAD) phasing. The hydroxyl groups at the C-1, -2, -3 and -4 position of fucose were individually substituted with a methylseleno group via a transacetalization reaction using MeSeCH2OBn or by an SN2 reaction with TolSe− equivalents to afford the corresponding MeSe-fucose. The three-dimensional structures of a fucose-binding lectin complexed with several of these MeSe-fucoses have been determined by SAD/MAD phasing by utilizing the diffraction of selenium in the bound MeSe-fucoses. |
| Databáze: | OpenAIRE |
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