Azlactone-based heterobifunctional linkers with orthogonal clickable groups: efficient tools for bioconjugation with complete atom economy

International audienceWe report the efficient synthesis of a series of new azlactone-based heterofunctional linkers bearing two orthogonal clickable groups that proceed with full atom economy. These new linkers comprise an azlactone (oxazolone) group that quickly reacts with amino groups in biologically relevant medium without byproduct elimination and a (bio)orthogonal handle which further undergoes facile and selective click reactions such as thiol–ene coupling, Diels–Alder or azide–alkyne cycloadditions. As an example, the application of this methodology to lysozyme PEGylation in aqueous medium is described

Spiro Iminosugars: Structural Diversity and Synthetic Strategies

International audienceFrom their discovery in the late 1960s, iminosugars have undergone an expansion from an area of science limited to a few researchers to a field that now attracts the interest of members of the whole synthetic organic chemistry community. Indeed, many tasks concern structural modifications of standard iminosugars in order to improve their biological and pharmacological properties. In this way, the introduction of an adjoining spirocycle afforded unprecedented polyhydroxy-azaspiranes, the structures and syntheses of which are presented in this chapter. Special attention is paid to the key steps involved in the generation of the pivotal quaternary spiro atom