English   español  
Please use this identifier to cite or link to this item: http://hdl.handle.net/10261/9291
Share/Impact:
Statistics
logo share SHARE logo core CORE   Add this article to your Mendeley library MendeleyBASE

Visualizar otros formatos: MARC | Dublin Core | RDF | ORE | MODS | METS | DIDL
Exportar a otros formatos:

Title

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

AuthorsCalveras Ibáñez, Jordi; Casas Brugulat, Josefina; Parella, Teodor; Joglar Tamargo, Jesús ; Clapés Saborit, Pere
KeywordsAldol reaction
Aldolases
Amino aldehydes
Hyacinthacines
Polyhydroxylated pyrrolizidine alkaloids
Issue Date17-Jul-2007
PublisherWiley-VCH
CitationAdvanced Synthesis & Catalysis 349(10) :1661-1666 (2007)
AbstractA 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.
Description6 páginas,1 figura, 2 esquemas, 2 tablas.
Publisher version (URL)http://dx.doi.org/10.1002/adsc.200700168
URIhttp://hdl.handle.net/10261/9291
DOI10.1002/adsc.200700168
ISSN1615-4169
Appears in Collections:(IQAC) Artículos
Files in This Item:
There are no files associated with this item.
Show full item record
Review this work
 

Related articles:


WARNING: Items in Digital.CSIC are protected by copyright, with all rights reserved, unless otherwise indicated.