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Título

Chemoenzymatic Synthesis and Inhibitory Activities of Hyacinthacines A1 and A2 Stereoisomers.

Autor Calveras Ibáñez, Jordi; Casas Brugulat, Josefina; Parella, Teodor; Joglar Tamargo, Jesús; Clapés Saborit, Pere
Palabras clave Aldol reaction
Aldolases
Amino aldehydes
Hyacinthacines
Polyhydroxylated pyrrolizidine alkaloids
Fecha de publicación 17-jul-2007
EditorWiley-VCH
Citación Advanced Synthesis & Catalysis 349(10) :1661-1666 (2007)
ResumenA novel straightforward chemoenzymatic procedure for the synthesis of hyacinthacine stereoisomers based on the aldol addition of dihydroxyacetone phosphate (DHAP) to N-Cbz-prolinal under catalysis by l-rhamnulose 1-phosphate aldolase from E. coli is presented. The synthesis is complemented by a simple and effective purification protocol consisting of ion-exchange chromatography on CM-sepharose. As examples, ( )-hyacinthacine A2 [the enantiomer of (+)-hyacinthacine A2], 7-deoxy- 2-epialexine (the enantiomer of 3-epihyacinthacine A2), ent-7-deoxyalexine (the enantiomer of 7-deoxyalexine) and 2-epihyacinthacine A2 were synthesized by these procedures and characterized for the first time. These new isomers were assayed as inhibitors of glycosidases. As a result, ( )-hyacinthacine A2 demonstrated to be a good inhibitor of a-d-glucosidase from rice whereas the natural enantiomer, hyacinthacine A2, was not. Moreover, a new family of inhibitors of a-l-rhamnosidase was uncovered.
Descripción 6 páginas,1 figura, 2 esquemas, 2 tablas.
Versión del editorhttp://dx.doi.org/10.1002/adsc.200700168
URI http://hdl.handle.net/10261/9291
DOI10.1002/adsc.200700168
ISSN1615-4169
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