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Title: | Chemoenzymatic Synthesis and Inhibitory Activities of Hyacinthacines A1 and A2 Stereoisomers. |
Authors: | Calveras Ibáñez, Jordi; Casas, Josefina ![]() ![]() ![]() |
Keywords: | Aldol reaction Aldolases Amino aldehydes Hyacinthacines Polyhydroxylated pyrrolizidine alkaloids |
Issue Date: | 17-Jul-2007 |
Publisher: | Wiley-VCH |
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 |
URI: | http://hdl.handle.net/10261/9291 |
DOI: | 10.1002/adsc.200700168 |
ISSN: | 1615-4169 |
Appears in Collections: | (IQAC) Artículos |
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