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

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• 作者：Junpei Shimabukuro^a ; ^c ; ¹ ; Hisayoshi Makyio^d ; ¹ ; Tatsuya Suzuki^a ; ^c ; Yosuke Nishikawa^d ; Masato Kawasaki^d ; Akihiro Imamura^a ; Hideharu Ishida^a ; ^b ; Hiromune Ando^a ; ^b ; ^c ; ^{hando@gifu-u.ac.jp} ; Ryuichi Kato^d ; ; Makoto Kiso^a ; ^c
• 关键词：Seleno-carbohydrate ; Carbohydrate-protein complex ; X-ray crystallography ; SAD/MAD phasing ; Lectin
• 刊名：Bioorganic & Medicinal Chemistry
• 出版年：2017
• 出版时间：1 February 2017
• 年：2017
• 卷：25
• 期：3
• 页码：1132-1142
• 全文大小：1150 K
• 卷排序：25

文摘

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.