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Chemoenzymatic Synthesis and Inhibitory Activities of Hyacinthacines A1 and A2 Stereoisomers.
|Authors:||Calveras Ibáñez, Jordi; Casas, Josefina ; Parella, Teodor; Joglar Tamargo, Jesús ; Clapés Saborit, Pere|
Polyhydroxylated pyrrolizidine alkaloids
|Citation:||Advanced Synthesis & Catalysis 349(10) :1661-1666 (2007)|
|Abstract:||A 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.|
|Description:||6 páginas,1 figura, 2 esquemas, 2 tablas.|
|Publisher version (URL):||http://dx.doi.org/10.1002/adsc.200700168|
|Appears in Collections:||(IQAC) Artículos|
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