A copper-catalyzed protocol furnishing -arylated sulfoximines has been developed via dual N-H/C-H activation. Arylalkyl- and less reactive diarylsulfoximines were efficiently coupled with privileged scaffolds like indolines, indoles, and -Ar-7-azaindoles. Sulfoximines based on medicinally relevant scaffolds (phenothiazine, dibenzothiophene, thioxanthenone) were also well tolerated. Detailed mechanistic studies indicate that the deprotometalation and protodemetalation step is the reversible step.
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CU(II)-catalyzed oxidation of Alzheimer's disease beta-amyloid peptide and related sequences: remarkably different selectivities of neurotoxic betaAP1-40 and non-toxic betaAP40-1.
Cell Mol Biol (Noisy-le-grand)
July 2003
Department of Pharmaceutical Chemistry, The University of Kansas, 2095 Constant Avenue, Lawrence, KS 66047, USA.
We investigated the CuII-catalyzed oxidation of beta-amyloid peptides betaAP10-20 and betaAP40-1 by tandem mass spectrometry and compared oxidation yields and selectivities to those for betaAP1-16, betaAP1-28 and betaAP1-40, which were obtained earlier (26). While betaAP1-16, betaAP1-28 and betaAP1-40 showed an almost exclusive oxidation of His residues to 2-oxo-histidine, the selectivity pattern is changed for betaAP10-20,which shows oxidation of His but also hydroxylation of Tyr and Phe. In contrast to betaAP1-40, the reverse sequence betaAP40-1 shows a strong selectivity for the hydroxylation of Tyr31 while only negligible His oxidation is observed at early time points.
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