RESUMO
Valienol-derived allylic C-1 bromides have been used as carbaglycosyl donors for α-xylo configured valienamine pseudodisaccharide synthesis. We synthesised valienamine analogues of the Glc(α1â3)Glc and Glc(α1â3)Man disaccharides representing the linkages cleaved by α-Glucosidase II in N-glycan biosynthesis. These (N1â3)-linked pseudodisaccharides were found to have some α-Glucosidase II inhibitory activity, while two other (N1â6)-linked valienamine pseudodisaccharides failed to inhibit the enzyme.
Assuntos
Cicloexenos/farmacologia , Inibidores Enzimáticos/farmacologia , Inibidores de Glicosídeo Hidrolases , Hexosaminas/farmacologia , Polissacarídeos/biossíntese , Biocatálise , Técnicas de Química Sintética , Cicloexenos/síntese química , Cicloexenos/química , Inibidores Enzimáticos/síntese química , Inibidores Enzimáticos/química , Hexosaminas/síntese química , Hexosaminas/química , Conformação Molecular , Polissacarídeos/química , Estereoisomerismo , Relação Estrutura-Atividade , alfa-Glucosidases/metabolismoRESUMO
Directly linked hydroporphyrin (chlorin) dimers were accessed regioselectively from bromochlorins. Versatile 15-borylated chlorins were prepared in excellent yield via Miyaura borylation. Suzuki coupling yielded meso-meso-linked homo- and heterodimers, and meso-ß-linked dimers. The photophysical and electrochemical properties of the dimers are reported.