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Consecutive intramolecular desymmetrization and kinetic resolution of 2-substituted N-phenoxycarbonylserinols have been achieved in one-pot by a single chiral catalyst, bisox)-CuCl2, to form oxazolidinones with remarkable enantioselectivities (94-99% ee) as tert-alkylamine building blocks. The process culminates in a dual-function of the chiral catalyst.

Asymmetric Synthesis of All-Carbon Quaternary Stereocenters via Desymmetrization of 2,2-Disubstituted 1,3-Propanediols. -The asymmetric monobenzoylation of symmetric diols is achieved with high enantioselectivities by use of the copper-catalyst derived from Pybox-ligand PBO. -(LEE, J. Y.; YOU, Y. S.; KANG*, S. H.; J. Am. Chem. Soc. 133 (2011) 6, 1772-1774, http://dx.

Ubiquitin proteasome system (UPS) on the mitochondrial is one of quality control systems that works as a first line of defense barrier against aggregated or misfolded proteins. In innate immunity formation of the MAVS(Mitochondrial anti-viral signaling protein) oligomers elicits robust type-I interferon induction upon viral infection and however, persistent RIG-I and MAVS complex rather leads to host immunopathology. We recently reported that mitochondria-resident E3 ligase, MARCH5, recognizes the oligomeric form of RIG-I and MAVS complex. MARCH5+/− mice and MARCH5 deficient immune cells exhibited low viral replication and elevated type-I interferon response to viral infection. MARCH5 bound RIG-I and MAVS complex only during viral infection when MAVS forms oligomer. MARCH5 mediates Lys-48-linked poly-ubiquitination chain addition to RIG-I and MAVS oligomer and induces the RIG-I/MAVS monomer. Next, we studies have suggested that a novel function of MARCH5 in inflammation signaling. Together, these data demonstrates that MARCH5 regulates oligomeric RIG-I and MAVS complex.

Catalyst. -A series of enantiopure oxazolidinones (III), useful tert.-alkylamine building blocks, is prepared in an one-pot manner by intramolecular desymmetrization of serinols (I) by a copper-catalyzed cyclization and a subsequent kinetic resolution of enantiomerically enriched hydroxymethyl-oxazolidinone intermediates (75-80% e.e.) by a benzoylation. -(YOU, Y. S.; KIM, T. W.; KANG*, S. H.; Chem. Commun. (Cambridge) 49 (2013) 83, 9669-9671, http://dx.