Synthesis of Enantiomeric Polyhydroxyalkylpyrrolidines from 1,3-Dipolar Cycloadducts. Evaluation as Inhibitors of a β-Galactofuranosidase

Enantiomeric 2,3,4-tris(hydroxyalkyl)-5-phenylpyrrolidines have been synthesized from the major cycloadducts obtained by the 1,3-dipolar cycloaddition of sugar enones with azomethine ylides derived from natural amino acids. Reduction of the ketone carbonyl group of the cycloadducts, which possess a...

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Autores principales:	Repetto, Evangelina, Varela, Oscar José
Publicado:	2016
Materias:	Ketones 1 ,3-Dipolarcycloaddition Azomethine ylides Bicyclic systems Carbonyl groups Natural amino acids No inhibitory activities Polyhydroxylated Trifluoroacetates Enantiomers azomethine ylide carbonyl derivative glycosidase ketone derivative pyrrolidine derivative bridged bicyclo compounds enzyme inhibitor exo-beta-D-galactofuranosidase Article chemical structure cycloaddition enantiomer enzyme inhibition hydrolysis molecule nonhuman oxidation Penicillium reduction substitution reaction synthesis antagonists and inhibitors conformation drug effect enzymology molecular model oxidation reduction reaction stereoisomerism Bridged Bicyclo Compounds Cycloaddition Reaction Enzyme Inhibitors Glycoside Hydrolases Hydrolysis Models, Molecular Molecular Conformation Oxidation-Reduction Pyrrolidines Stereoisomerism
Acceso en línea:	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00223263_v81_n10_p4179_OliveiraUdry http://hdl.handle.net/20.500.12110/paper_00223263_v81_n10_p4179_OliveiraUdry
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

id	paper:paper_00223263_v81_n10_p4179_OliveiraUdry
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spelling	paper:paper_00223263_v81_n10_p4179_OliveiraUdry2023-06-08T14:49:37Z Synthesis of Enantiomeric Polyhydroxyalkylpyrrolidines from 1,3-Dipolar Cycloadducts. Evaluation as Inhibitors of a β-Galactofuranosidase Repetto, Evangelina Varela, Oscar José Ketones 1 ,3-Dipolarcycloaddition Azomethine ylides Bicyclic systems Carbonyl groups Natural amino acids No inhibitory activities Polyhydroxylated Trifluoroacetates Enantiomers azomethine ylide carbonyl derivative glycosidase ketone derivative pyrrolidine derivative bridged bicyclo compounds enzyme inhibitor exo-beta-D-galactofuranosidase pyrrolidine derivative Article chemical structure cycloaddition enantiomer enzyme inhibition hydrolysis molecule nonhuman oxidation Penicillium reduction substitution reaction synthesis antagonists and inhibitors conformation drug effect enzymology molecular model oxidation reduction reaction stereoisomerism Bridged Bicyclo Compounds Cycloaddition Reaction Enzyme Inhibitors Glycoside Hydrolases Hydrolysis Models, Molecular Molecular Conformation Oxidation-Reduction Penicillium Pyrrolidines Stereoisomerism Enantiomeric 2,3,4-tris(hydroxyalkyl)-5-phenylpyrrolidines have been synthesized from the major cycloadducts obtained by the 1,3-dipolar cycloaddition of sugar enones with azomethine ylides derived from natural amino acids. Reduction of the ketone carbonyl group of the cycloadducts, which possess a basic structure of bicyclic 6-(menthyloxy)hexahydropyrano[4,3-c]pyrrol-7(6H)one, afforded a number of pyrrolidine-based bicyclic systems. A sequence of reactions, which involved hydrolysis of the menthyloxy substituent, reduction, N-protection, and degradative oxidation, afforded varied pyrrolidine structures having diverse configurations and patterns of substitution; in particular, polyhydroxylated derivatives have been obtained. The unprotected products were isolated as pyrrolidinium trifluoroacetates. Because of the furanose-like nature of the target trihydroxyalkyl pyrrolidines, these molecules have been evaluated as inhibitors of the β-galactofuranosidase from Penicillium fellutanum. The compounds showed practically no inhibitory activity for concentration of pyrrolidines in the range of 0.1-1.6 mM. © 2016 American Chemical Society. Fil:Repetto, E. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Varela, O. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2016 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00223263_v81_n10_p4179_OliveiraUdry http://hdl.handle.net/20.500.12110/paper_00223263_v81_n10_p4179_OliveiraUdry
institution	Universidad de Buenos Aires
institution_str	I-28
repository_str	R-134
collection	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic	Ketones 1 ,3-Dipolarcycloaddition Azomethine ylides Bicyclic systems Carbonyl groups Natural amino acids No inhibitory activities Polyhydroxylated Trifluoroacetates Enantiomers azomethine ylide carbonyl derivative glycosidase ketone derivative pyrrolidine derivative bridged bicyclo compounds enzyme inhibitor exo-beta-D-galactofuranosidase pyrrolidine derivative Article chemical structure cycloaddition enantiomer enzyme inhibition hydrolysis molecule nonhuman oxidation Penicillium reduction substitution reaction synthesis antagonists and inhibitors conformation drug effect enzymology molecular model oxidation reduction reaction stereoisomerism Bridged Bicyclo Compounds Cycloaddition Reaction Enzyme Inhibitors Glycoside Hydrolases Hydrolysis Models, Molecular Molecular Conformation Oxidation-Reduction Penicillium Pyrrolidines Stereoisomerism
spellingShingle	Ketones 1 ,3-Dipolarcycloaddition Azomethine ylides Bicyclic systems Carbonyl groups Natural amino acids No inhibitory activities Polyhydroxylated Trifluoroacetates Enantiomers azomethine ylide carbonyl derivative glycosidase ketone derivative pyrrolidine derivative bridged bicyclo compounds enzyme inhibitor exo-beta-D-galactofuranosidase pyrrolidine derivative Article chemical structure cycloaddition enantiomer enzyme inhibition hydrolysis molecule nonhuman oxidation Penicillium reduction substitution reaction synthesis antagonists and inhibitors conformation drug effect enzymology molecular model oxidation reduction reaction stereoisomerism Bridged Bicyclo Compounds Cycloaddition Reaction Enzyme Inhibitors Glycoside Hydrolases Hydrolysis Models, Molecular Molecular Conformation Oxidation-Reduction Penicillium Pyrrolidines Stereoisomerism Repetto, Evangelina Varela, Oscar José Synthesis of Enantiomeric Polyhydroxyalkylpyrrolidines from 1,3-Dipolar Cycloadducts. Evaluation as Inhibitors of a β-Galactofuranosidase
topic_facet	Ketones 1 ,3-Dipolarcycloaddition Azomethine ylides Bicyclic systems Carbonyl groups Natural amino acids No inhibitory activities Polyhydroxylated Trifluoroacetates Enantiomers azomethine ylide carbonyl derivative glycosidase ketone derivative pyrrolidine derivative bridged bicyclo compounds enzyme inhibitor exo-beta-D-galactofuranosidase pyrrolidine derivative Article chemical structure cycloaddition enantiomer enzyme inhibition hydrolysis molecule nonhuman oxidation Penicillium reduction substitution reaction synthesis antagonists and inhibitors conformation drug effect enzymology molecular model oxidation reduction reaction stereoisomerism Bridged Bicyclo Compounds Cycloaddition Reaction Enzyme Inhibitors Glycoside Hydrolases Hydrolysis Models, Molecular Molecular Conformation Oxidation-Reduction Penicillium Pyrrolidines Stereoisomerism
description	Enantiomeric 2,3,4-tris(hydroxyalkyl)-5-phenylpyrrolidines have been synthesized from the major cycloadducts obtained by the 1,3-dipolar cycloaddition of sugar enones with azomethine ylides derived from natural amino acids. Reduction of the ketone carbonyl group of the cycloadducts, which possess a basic structure of bicyclic 6-(menthyloxy)hexahydropyrano[4,3-c]pyrrol-7(6H)one, afforded a number of pyrrolidine-based bicyclic systems. A sequence of reactions, which involved hydrolysis of the menthyloxy substituent, reduction, N-protection, and degradative oxidation, afforded varied pyrrolidine structures having diverse configurations and patterns of substitution; in particular, polyhydroxylated derivatives have been obtained. The unprotected products were isolated as pyrrolidinium trifluoroacetates. Because of the furanose-like nature of the target trihydroxyalkyl pyrrolidines, these molecules have been evaluated as inhibitors of the β-galactofuranosidase from Penicillium fellutanum. The compounds showed practically no inhibitory activity for concentration of pyrrolidines in the range of 0.1-1.6 mM. © 2016 American Chemical Society.
author	Repetto, Evangelina Varela, Oscar José
author_facet	Repetto, Evangelina Varela, Oscar José
author_sort	Repetto, Evangelina
title	Synthesis of Enantiomeric Polyhydroxyalkylpyrrolidines from 1,3-Dipolar Cycloadducts. Evaluation as Inhibitors of a β-Galactofuranosidase
title_short	Synthesis of Enantiomeric Polyhydroxyalkylpyrrolidines from 1,3-Dipolar Cycloadducts. Evaluation as Inhibitors of a β-Galactofuranosidase
title_full	Synthesis of Enantiomeric Polyhydroxyalkylpyrrolidines from 1,3-Dipolar Cycloadducts. Evaluation as Inhibitors of a β-Galactofuranosidase
title_fullStr	Synthesis of Enantiomeric Polyhydroxyalkylpyrrolidines from 1,3-Dipolar Cycloadducts. Evaluation as Inhibitors of a β-Galactofuranosidase
title_full_unstemmed	Synthesis of Enantiomeric Polyhydroxyalkylpyrrolidines from 1,3-Dipolar Cycloadducts. Evaluation as Inhibitors of a β-Galactofuranosidase
title_sort	synthesis of enantiomeric polyhydroxyalkylpyrrolidines from 1,3-dipolar cycloadducts. evaluation as inhibitors of a β-galactofuranosidase
publishDate	2016
url	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00223263_v81_n10_p4179_OliveiraUdry http://hdl.handle.net/20.500.12110/paper_00223263_v81_n10_p4179_OliveiraUdry
work_keys_str_mv	AT repettoevangelina synthesisofenantiomericpolyhydroxyalkylpyrrolidinesfrom13dipolarcycloadductsevaluationasinhibitorsofabgalactofuranosidase AT varelaoscarjose synthesisofenantiomericpolyhydroxyalkylpyrrolidinesfrom13dipolarcycloadductsevaluationasinhibitorsofabgalactofuranosidase
_version_	1768543933182246912

Synthesis of Enantiomeric Polyhydroxyalkylpyrrolidines from 1,3-Dipolar Cycloadducts. Evaluation as Inhibitors of a β-Galactofuranosidase

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