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Fructose-6-phosphate aldolase in organic synthesis: preparation of D-fagomine, N-alkylated derivatives, and preliminary biological assays

AuthorsCastillo Expósito, José A.; Calveras Ibáñez, Jordi; Casas, Josefina ; Mitjans, Montserrat; Vinardell, M. Pilar ; Parella, Teodor; Inoue, Tomoyuki; Sprenger, Georg A.; Joglar Tamargo, Jesús ; Clapés Saborit, Pere
Issue Date29-Nov-2006
PublisherAmerican Chemical Society
CitationOrganic Letters 8(26): 6067-6070 (2006)
AbstractD-Fructose-6-phosphate aldolase (FSA) mediates a novel straightforward two-step chemo-enzymatic synthesis of D-fagomine and some of its N-alkylated derivatives in 51% isolated yield and 99% de. The key step is the FSA-catalyzed aldol addition of simple dihydroxyacetone (DHA) to N-Cbz-3-aminopropanal. The use of FSA greatly simplifies the enzymatic procedures that used dihydroxyacetonephosphate or DHA/esters.tives synthesized elicited antifungal and antibacterial activity as well as enhanced inhibitory activity, and selectivity against β-galactosidase and α-glucosidase.
Description4 pages, 2 figures.-- PMID: 17165931 [PubMed].-- Printed version published Dec 21, 2006.
Supporting information available at: http://pubs.acs.org/doi/suppl/10.1021/ol0625482
Publisher version (URL)http://dx.doi.org/10.1021/ol0625482
Appears in Collections:(IQAC) Artículos
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