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1.
J Enzyme Inhib Med Chem ; 30(3): 472-8, 2015 Jun.
Article in English | MEDLINE | ID: mdl-25140865

ABSTRACT

Insight into the structure and inhibition mechanism of O-ß-d-glucosidases by deoxa-pyranosylamine type inhibitors is provided by X-ray analysis of complexes between raucaffricine and strictosidine glucosidases and N-(cyclohexylmethyl)-, N-(cyclohexyl)- and N-(bromobenzyl)-ß-d-gluco-1,5-deoxa-pyranosylamine. All inhibitors anchored exclusively in the catalytic active site by competition with appropriate enzyme substrates. Thus facilitated prospective elucidation of the binding networks with residues located at <3.9 Å distance will enable the development of potent inhibitors suitable for the production of valuable alkaloid glucosides, raucaffricine and strictosidine, by means of synthesis in Rauvolfia serpentina cell suspension cultures.


Subject(s)
Cyclopentanes/pharmacology , Glucosidases/antagonists & inhibitors , Glucosidases/metabolism , Sugar Alcohols/pharmacology , Binding Sites/drug effects , Cyclopentanes/chemistry , Dose-Response Relationship, Drug , Glucosidases/chemistry , Ligands , Models, Molecular , Molecular Structure , Rauwolfia/cytology , Rauwolfia/enzymology , Structure-Activity Relationship , Sugar Alcohols/chemistry
2.
Org Lett ; 10(19): 4171-4, 2008 Oct 02.
Article in English | MEDLINE | ID: mdl-18754589

ABSTRACT

The attachment of multiple triazole moieties and perfluoroalkyl chains to TEMPO promotes emulsion formation in dichloromethane/water, giving a highly active and easily recoverable catalyst for the oxidation of alcohols.

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