Development of α1, 6-fucosyltransferase inhibitors through the diversity-oriented syntheses of GDP-fucose mimics using the coupling between alkyne and sulfonyl azide. Issue 11 (1st June 2017)

• Record Type: Journal Article
• Authors: Manabe, Yoshiyuki; Kasahara, Satomi; Takakura, Yohei; Yang, Xiaoxiao; Takamatsu, Shinji; Kamada, Yoshihiro; Miyoshi, Eiji; Yoshidome, Daisuke; Fukase, Koichi
• Is Part Of: Bioorganic & medicinal chemistry. Volume 25:Issue 11(2017)
• Page Start: 2844
• Page End: 2850
• Publication Date: 2017-06-01
• Subjects: Glycosyltransferase inhibitor -- α1, 6-Fucosyltransferase -- Diversity-oriented synthesis -- Sulfonyl azide; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; Biochemistry -- Periodicals; Chemistry, Clinical -- Periodicals; Chemistry, Organic -- Periodicals; Chimie bio-organique -- Périodiques; Chimie pharmaceutique -- Périodiques; 615.19
• DOI: 10.1016/j.bmc.2017.02.036
• Languages: English
• ISSNs: 0968-0896

Abstract

Graphical abstract: Abstract: We developed α1, 6-fucosyltransferase (FUT8) inhibitors through a diversity-oriented synthesis. The coupling reaction between the fucose unit containing alkyne and the guanine unit containing sulfonyl azide under various conditions afforded a series of Guanosine 5′-diphospho-β-l -fucose (GDP-fucose) analogs. The synthesized compounds displayed FUT8 inhibition activity. A docking study revealed that the binding mode of the inhibitor synthesized with FUT8 was similar to that of GDP-fucose.