Strain??Promoted Alkyne–Azide Cycloadditions (SPAAC) Reveal New Features of Glycoconjugate Biosynthesis

NE Mbua, J Guo, MA Wolfert, R Steet…

Index: Mbua, Ngalle Eric; Guo, Jun; Wolfert, Margreet A.; Steet, Richard; Boons, Geert-Jan ChemBioChem, 2011 , vol. 12, # 12 p. 1912 - 1921

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Citation Number: 81

Abstract

Abstract We have shown that 4-dibenzocyclooctynol (DIBO), which can easily be obtained by a streamlined synthesis approach, reacts exceptionally fast in the absence of a Cu I catalyst with azido-containing compounds to give stable triazoles. Chemical modifications of DIBO, such as oxidation of the alcohol to a ketone, increased the rate of strain promoted azide–alkyne cycloadditions (SPAAC). Installment of a ketone or oxime in the cyclooctyne ...