Ana Bellomo

Chemoenzymatic Synthesis and Biological Evaluation of (−)‐Conduramine C‐4

Abstract Previously unreported (−)‐conduramine C‐4 was synthesized in six steps from a bacterial bromobenzene metabolite in 23% overall yield. The chemoenzymatic route involved toluene dioxygenase dihydroxylation, β‐epoxidation, epoxide ring‐opening, Staudinger reduction, radical debromination, and Amberlite‐ catalyzed hydrolysis. (−)‐Conduramine C‐4 and other related compounds synthesised were assayed for galactosidase‐activity inhibition against β‐D‐galactoside galactohidrolase isolated from Aspergillus oryzae.

Enantiospecific synthesis and insect feeding activity of sulfur-containing cyclitols

The first syntheses of two deoxythiocyanocyclitols (4-deoxy-4-thiocyano-L-chiro-inositol and deoxythiocyanoconduritol F) and two deoxysulfonylcyclitol acetals are reported by a chemoenzymatic enantioselective route. The compounds were prepared by a sequence of enzymatic and ruthenium-catalyzed dihydroxylations, and the results were studied regarding reaction conditions and co-catalyst for different derivatives. The new compounds were included in a minilibrary of deoxygenated cyclitols and evaluated for their capacity to influence the feeding behavior of Epilachna paenulata (Coleoptera: Coccinellidae), a common pest of the Curcubitaceae crops.

Expanding cyclitol structural diversity by biocatalysis and metalocatalysis. A click chemistry approach

The palladium catalyzed cross-coupling reaction of phenyltrifluoroborate with a chemoenzymatically derived bromoazidoconduritol, combined with 1,3-dipolar cycloaddition, with a variety of alkynes is described. Fourteen new compounds were synthesized in moderate to good yields. The click chemistry reaction can be effected by using sodium ascorbate and CuSO4 · 5H2O as catalyst in toluene–H2O at room temperature.

Antifungal Activity of a Library of Cyclitols and Related Compounds

Affiliations: Roy and Diana Vagelos Laboratories, Penn/Merck Laboratory for High-Throughput Experimentation, Department of Chemistry, University of Pennsylvania, United States. Depto. de Quimica Organica, Facultad. de Quimica, Universidad de la Republica, UdelaR, Montevideo, Uruguay. Farmacognosia, Facultad de Ciencias Bioquimicas y Farmaceuticas, Universidad Nacional de Rosario, Rosario, Argentina. Departamento de Farmacia, Faculdade de Ciencias Farmaceuticas, Universidade de Sao Paulo, Sao Paulo, SP, Brazil.